EP4188976A1 - Rheology-modifying difunctional compound - Google Patents

Rheology-modifying difunctional compound

Info

Publication number
EP4188976A1
EP4188976A1 EP21758397.0A EP21758397A EP4188976A1 EP 4188976 A1 EP4188976 A1 EP 4188976A1 EP 21758397 A EP21758397 A EP 21758397A EP 4188976 A1 EP4188976 A1 EP 4188976A1
Authority
EP
European Patent Office
Prior art keywords
compound
carbon atoms
alkoxylated
polyethoxylated
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP21758397.0A
Other languages
German (de)
French (fr)
Inventor
Yves MATTER
Denis Ruhlmann
Jean-Marc Suau
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Coatex SAS
Original Assignee
Coatex SAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Coatex SAS filed Critical Coatex SAS
Publication of EP4188976A1 publication Critical patent/EP4188976A1/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C265/00—Derivatives of isocyanic acid
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/43—Thickening agents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C263/00—Preparation of derivatives of isocyanic acid
    • C07C263/16—Preparation of derivatives of isocyanic acid by reactions not involving the formation of isocyanate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/02—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from isocyanates with formation of carbamate groups
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C271/06—Esters of carbamic acids
    • C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C271/36—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/227—Catalysts containing metal compounds of antimony, bismuth or arsenic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
    • C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/08—Polyurethanes from polyethers
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09D105/00—Coating compositions based on polysaccharides or on their derivatives, not provided for in groups C09D101/00 or C09D103/00
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    • C09D125/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Coating compositions based on derivatives of such polymers
    • C09D125/02—Homopolymers or copolymers of hydrocarbons
    • C09D125/04—Homopolymers or copolymers of styrene
    • C09D125/08—Copolymers of styrene
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    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C09D17/001—Pigment pastes, e.g. for mixing in paints in aqueous medium
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    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C09D17/004—Pigment pastes, e.g. for mixing in paints containing an inorganic pigment
    • C09D17/007—Metal oxide
    • C09D17/008—Titanium dioxide
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    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02—Emulsion paints including aerosols
    • C09D5/024—Emulsion paints including aerosols characterised by the additives
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    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/61—Additives non-macromolecular inorganic
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    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
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Definitions

  • the invention relates to a difunctional rheology modifying compound.
  • the invention also provides an aqueous composition comprising a difunctional compound according to the invention as well as a method for controlling the viscosity of an aqueous composition by means of the difunctional compound according to the invention.
  • aqueous coating compositions and in particular for aqueous paint or varnish compositions, it is necessary to control the viscosity both for low or medium shear gradients and for high shear gradients. Indeed, during its preparation, its storage, its application or its drying, a paint formulation undergoes many constraints requiring particularly complex rheological properties.
  • the pigment particles tend to settle by gravity. Stabilizing the dispersion of these pigment particles then requires having a paint formulation whose viscosity is high at very low shear gradients corresponding to the limit speed of the particles.
  • Paint pick-up is the amount of paint carried away by means of an application tool, such as a brush, brush or roller for example.
  • the tool immersed and then removed from the paint pot carrying a large quantity of paint will avoid having to be reloaded more frequently. Paint pick-up is an increasing function of viscosity.
  • the equivalent shear rate calculation is a function of the paint flow rate for a particular thickness of paint on the tool.
  • the paint formulation should therefore also have a high viscosity at low or medium shear rates.
  • a high filling power of the paint must be sought so that when it is applied to a substrate, a large quantity of paint is deposited during each pass. A high filling power then makes it possible to obtain a greater wet film during each pass of the tool.
  • a high viscosity of the paint formulation must therefore be sought at high shear rates. High viscosity at high shear rates will also reduce or eliminate the risk of spattering or dripping during paint application.
  • Reduced viscosity at low to medium shear rates will also provide a good taut appearance after application of paint, especially paint monolayer, on a substrate whose coated surface will then present a very regular appearance, without bumps or hollows. The final visual appearance of the dry film is then much better.
  • the paint after being deposited on a surface, in particular a vertical surface, the paint should not form a run. It is then necessary for the paint formulation to have a high viscosity at low and medium shear rates.
  • the paint should have a significant leveling capacity. Reduced viscosity at low to medium shear rates of the paint formulation is then required.
  • JPH06322392 describes detergent dissolution additives which are prepared from diols or polyethers.
  • Document EP0295031 discloses a surfactant compound for a crosslinkable isocyanate resin prepared from polyethers.
  • Document US4301083 relates to the preparation of polyether derivatives from halides.
  • Compounds of the HEUR type hydrophobically modified ethoxylated urethanes or ethoxylated and hydrophobically modified urethanes
  • rheology modifying agents are known as rheology modifying agents.
  • the known HEUR-type compounds do not always make it possible to provide a satisfactory solution.
  • the rheology modifying compounds of the state of the art do not always allow effective control of the viscosity or do not always allow the compromise between Stormer viscosity (measured at low or medium shear gradients and expressed in KU units) and ICI viscosity (measured at high or very high shear rates and expressed in s 1 ).
  • the known rheology modifier compounds do not always make it possible to increase the ICI viscosity/Stormer viscosity ratio.
  • the difunctional compound according to the invention makes it possible to provide a solution to all or part of the problems of the rheology modifying agents of the state of the art.
  • the invention provides a difunctional compound T prepared by reacting: a. a molar equivalent of at least one non-alkoxylated compound (a) chosen from:
  • - branched aliphatic monoisocyanate compounds (a2) comprising from 6 to 40 non-alkoxylated carbon atoms
  • - cycloaliphatic monoisocyanate (a3) compounds comprising from 6 to 40 non-alkoxylated carbon atoms
  • alO polyaromatic monohaloalkylene
  • polyaromatic monoalcohols (b5) comprising from 10 to 80 polyethoxylated carbon atoms comprising from 80 to 500 oxyethylene groups.
  • the compounds (al) to (a5) result from the prior reaction of a diisocyanate compound and, respectively:
  • cycloaliphatic monoalcohol comprising 6 to 40 non-alkoxylated carbon atoms
  • polyaromatic monoalcohol comprising 10 to 80 non-alkoxylated carbon atoms.
  • the diisocyanate compounds are symmetrical diisocyanate compounds or else unsymmetrical diisocyanate compounds.
  • Symmetrical diisocyanate compounds include two isocyanate groups that have the same reactivity.
  • Unsymmetrical diisocyanate compounds include two isocyanate groups that have different reactivities.
  • the diisocyanate compound is a compound in which the two isocyanate groups have different reactivities.
  • the diisocyanate compound can be chosen from unsymmetrical diisocyanate compounds, preferably IPDI.
  • the diisocyanate compound can also be 2,6 TDI.
  • the diisocyanate compound can be chosen from:
  • H12MDI methylene bis(4-cyclohexylisocyanate)
  • HDI hexamethylene diisocyanate
  • PDI pentamethylene diisocyanate
  • the difunctional compound T is prepared from at least one compound (a1) to (a5) comprising an isocyanate group or from at least one compound (a6) to (a1O) comprising a halogen atom and a compound (b) capable of reacting with this isocyanate group or with this halogen atom and comprising a hydrocarbon chain - saturated, unsaturated or aromatic - combined with a polyethoxylated chain.
  • this reactive compound (b) is a monohydroxylated compound.
  • the condensation of compounds (a1) to (a5) and of compound (b) is carried out in the presence of a catalyst.
  • This catalyst can be chosen from an amine, preferably 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), a derivative of a metal chosen from Al, Bi, Sn, Hg, Pb, Mn, Zn, Zr, Ti. Traces of water can also participate in the catalysis of the reaction.
  • DBU 1,8-diazabicyclo[5.4.0]undec-7-ene
  • metal derivatives a derivative selected from dibutyl bismuth dilaurate, dibutyl bismuth diacetate, dibutyl bismuth oxide, bismuth carboxylate, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin oxide, a derivative of mercury is preferred.
  • the preferred metal derivative is selected from a Bi derivative, an Sn derivative and a Ti derivative.
  • the condensation of the compounds (a6) to (alO) and of the compound (b) is carried out in the presence of a catalyst, in particular a base, for example a strong base, such as KOH, NaOH .
  • a catalyst in particular a base, for example a strong base, such as KOH, NaOH .
  • the reaction implements a single compound (a) or else the reaction implements two or three different compounds (a).
  • the monohalogen compound is chosen from a chlorine compound, a bromine compound, an iodine compound and combinations thereof, preferably the monohalogen compound is a bromine compound.
  • the monoaromatic monohaloalkylene compounds (a9) are compounds comprising a single monohalogenated aromatic group via an alkylene group.
  • the halogen atom is not directly carried by the aromatic group.
  • the polyaromatic monohaloalkylene (alO) compounds are compounds comprising at least two groups aromatics, at least one of which is monohalogenated via an alkylene group.
  • the halogen atom is not directly carried by an aromatic group.
  • compound (a) is such that:
  • the hydrocarbon chain of compound (al) or of compound (a6) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 16 carbon atoms, more preferably compound (al) or the compound (a6) is chosen from non-alkoxylated n-octanyl, non-alkoxylated n-decanyl, non-alkoxylated n-dodecanyl, non-alkoxylated n-hexadecanyl, or
  • the hydrocarbon chain of compound (a2) or of compound (a7) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 16 carbon atoms, more preferably compound (a2) or the compound (a7) is chosen from non-alkoxylated ethyl-hexanyl, non-alkoxylated iso-octanyl, non-alkoxylated iso-nonanyl, non-alkoxylated iso-decanyl, non-alkoxylated propyl-heptanyl, non-alkoxylated butyl-octanyl, non-alkoxylated iso-dodecanyl, non-alkoxylated iso-hexadecanyl, an alkyl group derived from a non-alkoxylated oxo alcohol, an alkyl group derived from a non-alkoxylated Guerbet alcohol, or
  • the hydrocarbon chain of compound (a3) or of compound (a8) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 20 carbon atoms, more preferably compound (a3) or the compound (a8) is chosen from non-alkoxylated ethyl-cyclohexanyl, non-alkoxylated n-nonyl-cyclohexanyl, non-alkoxylated n-dodecyl-cyclohexanyl, or
  • the hydrocarbon chain of compound (a4) or of compound (a9) comprises from 12 to 30 carbon atoms or from 12 to 22 carbon atoms, preferably compound (a4) or compound (a9) is chosen from n- non-alkoxylated pentadocecyl-phenyl or
  • the hydrocarbon chain of the compound (a5) or of the compound (alO) comprises from 10 to 60 carbon atoms, preferably the compound (a5) or the compound (alO) is chosen from non-alkoxylated naphthyl, non-alkoxylated distyryl-phenyl alkoxylated, non-alkoxylated tristyryl-phenyl, non-alkoxylated pentastyryl-cumyl-phenyl.
  • monoalcohols are compounds comprising a single hydroxyl group (OH) which is terminal.
  • the polyethoxylated monoalcohols are compounds comprising a hydrocarbon chain which comprises several oxyethylene groups and a terminal hydroxyl (OH) group.
  • the polyethoxylated monoalcohols are compounds of formula R-(LO) n -H in which R represents a hydrocarbon chain, n represents the number of polyethoxylations and L, identical or different, independently represents a linear alkylene group comprising 2 carbon atoms.
  • the non-alkoxylated monoalcohols are compounds comprising a hydrocarbon chain and a single terminal hydroxyl (OH) group.
  • the non-alkoxylated monoalcohols are compounds of formula R'-OH in which R' represents a hydrocarbon chain.
  • the number of carbon atoms defining the monoalcohols (b1) to (b5) therefore corresponds to the number of carbon atoms of the groups R or R′.
  • the polyethoxylated monoalcohols (b1) and (b3) comprise from 105 to 400 ethoxylated groups or from 105 to 200 ethoxylated groups.
  • the polyethoxylated monoalcohols (b2), (b4) and (b5) comprise from 80 to 400 ethoxylated groups or from 100 to 200 ethoxylated groups.
  • the polyethoxylated compounds (b) used may comprise a number of identical or different ethoxylated groups.
  • the ethoxylated groups are oxyethylene groups (-CH2CH2O-).
  • compound T is a compound comprising ethoxylated groups.
  • compound T has a degree of polyethoxylation of between 100 and 500 or between 100 and 502. The degree of polyethoxylation defines the number of ethoxylated groups included in this compound.
  • compound (b) is such that: - the hydrocarbon chain of compound (bl) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 16 carbon, more preferably the compound (bl) is chosen from polyethoxylated n-octanol, polyethoxylated n-decanol, polyethoxylated n-dodecanol, polyethoxylated n-hexadecanol, or - the hydrocarbon chain of the compound (b2) comprises from 6 to 30 atoms of carbon, preferably from 6 to 20 carbon atoms or from 8 to 16 carbon atoms, more preferably compound (b2) is chosen from polyethoxylated ethyl-hexanol, polyethoxylated iso-octanol, polyethoxylated iso-nonanol, polyethoxylated iso-decanol, polyethoxylated propy
  • the hydrocarbon chain of compound (b3) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 20 carbon atoms, more preferably compound (b3) is chosen from ethyl-cyclohexanol polyethoxylated, polyethoxylated n-nonyl-cyclohexanol, polyethoxylated n-dodecyl-cyclohexanol, or
  • the hydrocarbon chain of compound (b4) comprises from 12 to 30 carbon atoms or from 12 to 22 carbon atoms, preferably compound (b4) is chosen from polyethoxylated n-pentadocecyl-phenol or
  • the hydrocarbon chain of compound (b5) comprises from 10 to 60 carbon atoms, preferably compound (b5) is chosen from polyethoxylated naphthol, polyethoxylated distyryl-phenol, polyethoxylated tristyryl-phenol, polyethoxylated pentastyryl-cumyl-phenol.
  • the compound T is prepared by means of a monoalcohol and in the absence of diol or triol or in the absence of a compound comprising at least two hydroxyl groups (OH).
  • the invention also relates to a method for preparing this compound.
  • the invention provides a method for preparing a difunctional compound T by reaction: a. a molar equivalent of at least one non-alkoxylated compound (a) chosen from:
  • - monohalogenated cycloaliphatic compounds comprising from 6 to 40 non-alkoxylated carbon atoms
  • - monoaromatic monohaloalkylene compounds comprising from 7 to 30 non-alkoxylated carbon atoms
  • alO polyaromatic monohaloalkylene
  • polyaromatic monoalcohols (b5) comprising from 10 to 80 polyethoxylated carbon atoms comprising from 80 to 500 oxyethylene groups.
  • the condensation of the compounds (al) to (a5) and (b) is carried out in the presence of a catalyst.
  • the reaction is catalyzed by means of an amine, preferably by means of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), or at least one derivative of a metal chosen from Al, Bi, Sn, Hg, Pb, Mn, Zn, Zr, Ti. Traces of water can also participate in the catalysis of the reaction.
  • metal derivatives a derivative selected from dibutyl bismuth dilaurate, dibutyl bismuth diacetate, dibutyl bismuth oxide, bismuth carboxylate, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin oxide, a derivative of mercury, a derivative of lead, zinc salts, manganese salts, a compound comprising chelated zirconium, a compound comprising chelated aluminium.
  • the preferred metal derivative is selected from a Bi derivative, an Sn derivative and a Ti derivative.
  • the condensation of the compounds (a6) to (alO) and of the compound (b) is carried out in the presence of a catalyst, in particular a base, for example a strong base, such as KOH, NaOH .
  • a catalyst in particular a base, for example a strong base, such as KOH, NaOH .
  • the condensation of compounds (a) and (b) is carried out in an organic solvent.
  • organic solvents are solvents non-reactive with the isocyanate functions or with the halogen atoms of compound (a), in particular the solvents chosen from hydrocarbon solvents (in particular Cs to C30 petroleum fractions), aromatic solvents (in particular toluene and its derivatives) and their combinations.
  • the condensation is carried out directly with the various reagents or else is carried out in toluene.
  • a solution of the compound is obtained in an organic solvent.
  • Such a solution can be implemented directly.
  • the organic solvent can be separated and the compound T dried.
  • Such a compound T according to the invention, which is dried, can then be implemented in solid form, for example in the form of powder or granules.
  • the invention also relates to an aqueous composition comprising at least one difunctional compound T according to the invention.
  • the invention also relates to an aqueous composition comprising at least one difunctional compound T prepared according to the preparation method according to the invention.
  • the difunctional compound according to the invention is a compound having a hydrophilic character. It can be formulated in an aqueous medium.
  • the aqueous composition according to the invention may also comprise at least one additive, in particular an additive chosen from:
  • amphiphilic compound in particular a surfactant compound, preferably a hydroxylated surfactant compound, for example alkyl-polyalkylene glycol, in particular alkyl-polyethylene glycol and alkyl-polypropylene glycol;
  • a polysaccharide derivative for example cyclodextrin, cyclodextrin derivative, polyethers, alkyl-glucosides;
  • solvents in particular coalescence solvents, and hydrotropic compounds, for example glycol, butylglycol, butyldiglycol, monopropyleneglycol, ethyleneglycol, ethylenediglycol, Dowanol products whose CAS number is 34590-94-8), Texanol products whose CAS number is 25265-77 -4);
  • the invention also provides an aqueous formulation which can be used in many technical fields.
  • the aqueous formulation according to the invention comprises at least one composition according to the invention and may comprise at least one organic or inorganic pigment or organic, organo-metallic or inorganic particles, for example calcium carbonate, talc, kaolin, mica, silicates , silica, metal oxides, including titanium dioxide, iron oxides.
  • the aqueous formulation according to the invention may also comprise at least one agent chosen from a particle spacer, a dispersing agent, a steric stabilizing agent, an electrostatic stabilizing agent, an opacifying agent, a solvent, a coalescing agent, a antifoam, a preservative, a biocidal agent, a spreading agent, a thickening agent, a film-forming copolymer and mixtures thereof.
  • at least one agent chosen from a particle spacer, a dispersing agent, a steric stabilizing agent, an electrostatic stabilizing agent, an opacifying agent, a solvent, a coalescing agent, a antifoam, a preservative, a biocidal agent, a spreading agent, a thickening agent, a film-forming copolymer and mixtures thereof.
  • the formulation according to the invention can be implemented in numerous technical fields.
  • the formulation according to the invention can be a coating formulation.
  • the formulation according to the invention is an ink formulation, an adhesive formulation, a varnish formulation, a paint formulation, for example decorative paint or industrial paint.
  • the formulation according to the invention is a paint formulation.
  • the invention also provides a concentrated aqueous pigment paste comprising at least one difunctional compound T according to the invention or at least one difunctional compound T prepared according to the preparation method according to the invention and at least one organic or inorganic colored pigment.
  • the difunctional compound according to the invention has properties allowing it to be used to modify or control the rheology of the medium comprising it.
  • the invention also provides a method for controlling the viscosity of an aqueous composition.
  • This viscosity control method according to the invention comprises the addition of at least one difunctional compound T according to the invention in an aqueous composition.
  • This viscosity control method can also comprise the addition of at least one difunctional compound T prepared according to the preparation method according to the invention.
  • the viscosity control method according to the invention is implemented by means of an aqueous composition according to the invention.
  • the method for controlling the viscosity according to the invention is implemented by means of an aqueous formulation according to the invention.
  • the preferred, particular or advantageous characteristics of the difunctional compound T according to the invention define aqueous compositions according to the invention, formulations according to the invention, pigment pastes and viscosity control methods which are also preferred, particular or advantageous. .
  • Example 1 preparation of difunctional compounds according to the invention
  • Example 1-1 preparation of a compound T1 according to the invention
  • reaction mixture is left under stirring for 15 minutes. Then, it is verified that the theoretical rate of NCO functions is reached by a return dosing. 1 g of the reaction medium is taken, to which an excess of dibutylamine (1 molar for example) is added, which reacts with the isocyanate functions present in the medium. The unreacted dibutylamine is then dosed with hydrochloric acid (1 N for example). The quantity of isocyanate functions present in the reaction medium can then be deduced therefrom. Then, the contents of container 2 are poured into container 1. Stirring is maintained for 60 minutes at 90 ⁇ 1°C. It is checked that the level of NCO function is zero indicating the end of the reaction.
  • the reaction is prolonged for periods of 15 minutes until the reaction is complete.
  • the compound T1 obtained is formulated in water with the addition of 1,000 ppm of a biocidal agent (Biopol SMV Chemipol) and 1,000 ppm of an anti-foaming agent (Tego 1488 Evonik).
  • a composition 1 consisting of 20% by mass of compound T1 according to the invention and 80% by mass of water is obtained.
  • Example 1-2 preparation of a compound T2 according to the invention
  • 15.67 g of IPDI are introduced into a 100 mL three-necked glass flask (receptacle 2), to which 400 ppm of bismuth carboxylate catalyst are added.
  • the medium is purged with nitrogen and then heated to 50°C. When this temperature is reached, 11.16 g of decanol are gradually introduced. After complete addition, the reaction mixture is left under stirring for 15 minutes. Then, it is verified that the theoretical rate of NCO functions is reached by a return dosing.
  • the contents of container 2 are poured into container 1. Stirring is maintained for 60 minutes at 90 ⁇ 1°C. It is checked that the NCO function level is zero indicating the end of the reaction. If this is non-zero, the reaction is prolonged for periods of 15 minutes until the reaction is complete. When the rate reaches zero, the compound T2 obtained is formulated in water with the addition of 1,000 ppm of a biocidal agent (Biopol SMV Chemipol) and 1,000 ppm of an anti-foaming agent (Tego 1488 Evonik). A composition 2 is obtained consisting of 20% by mass of compound T2 according to the invention and 80% by mass of water.
  • a biocidal agent Biopol SMV Chemipol
  • an anti-foaming agent Tego 1488 Evonik
  • Example 1-3 preparation of a compound T3 according to the invention
  • Example 1-5 preparation of a compound T5 according to the invention
  • Example 2 preparation of paint formulations according to the invention
  • the paint formulations F1 to F5 according to the invention are prepared from aqueous compositions 1 to 5 respectively of difunctional compounds T1 to T5 according to the invention. All the ingredients and proportions (% by mass) used are presented in Table 1.
  • the difunctional compounds according to the invention are very effective in obtaining excellent viscosities at low and medium shear gradients for paint compositions.
  • Example 4 Characterization of Paint Formulations According to the Invention
  • the Cone Plane viscosity or ICI viscosity measured at high shear gradient, was determined 24 hours after their preparation and at room temperature. (pi in mPa.s), using a Cone & Plate Research Equipment London (REL) viscometer with a measurement scale of 0 to 5 poises, and the Stormer viscosity, measured at a medium shear rate (pS in Krebs Units or KU), using the standard module of a Brookfield KU-2 viscometer.
  • the properties of the paint formulations are shown in Table 3. Table 3
  • the difunctional compounds according to the invention make it possible to prepare paint formulations whose viscosities are particularly well controlled.
  • the viscosity mi is particularly high and the ratio mi/ps is then excellent.
  • the compounds according to the invention allow an excellent compromise between the viscosity at high shear gradient and the viscosity at low shear gradient.

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Abstract

The invention relates to a rheology-modifying difunctional compound. The invention also provides an aqueous composition containing a difunctional compound according to the invention and a method for controlling the viscosity of an aqueous composition using the difunctional compound according to the invention.

Description

COMPOSÉ DIFONCTIONNEL MODIFICATEUR DE RHÉOLOGIE DIFUNCTIONAL RHEOLOGY MODIFIER COMPOUND
L’invention concerne un composé difonctionnel modificateur de rhéologie. L’invention fournit également une composition aqueuse comprenant un composé difonctionnel selon l’invention ainsi qu’une méthode de contrôle de la viscosité d’une composition aqueuse au moyen du composé difonctionnel selon l’invention. The invention relates to a difunctional rheology modifying compound. The invention also provides an aqueous composition comprising a difunctional compound according to the invention as well as a method for controlling the viscosity of an aqueous composition by means of the difunctional compound according to the invention.
De manière générale pour les compositions aqueuses de revêtement, et en particulier pour les compositions aqueuses de peinture ou de vernis, il est nécessaire de contrôler la viscosité tant pour de faibles ou moyens gradients de cisaillement que pour des gradients de cisaillement élevés. En effet, au cours de sa préparation, de son stockage, de son application ou de son séchage, une formulation de peinture subit de nombreuses contraintes nécessitant des propriétés rhéologiques particulièrement complexes. In general, for aqueous coating compositions, and in particular for aqueous paint or varnish compositions, it is necessary to control the viscosity both for low or medium shear gradients and for high shear gradients. Indeed, during its preparation, its storage, its application or its drying, a paint formulation undergoes many constraints requiring particularly complex rheological properties.
Lors du stockage de la peinture, les particules de pigment tendent à sédimenter par gravité. Stabiliser la dispersion de ces particules de pigment nécessite alors de disposer d’une formulation de peinture dont la viscosité est élevée à de très faibles gradients de cisaillement correspondant à la vitesse limite des particules. During paint storage, the pigment particles tend to settle by gravity. Stabilizing the dispersion of these pigment particles then requires having a paint formulation whose viscosity is high at very low shear gradients corresponding to the limit speed of the particles.
La prise de peinture est la quantité de peinture emportée au moyen d’un outil d’application, tel qu’un pinceau, une brosse ou un rouleau par exemple. L’outil plongé puis retiré du pot de peinture emportant une quantité élevée de peinture évitera de devoir être rechargé plus fréquemment. La prise de peinture est fonction croissante de la viscosité. Le calcul du gradient de cisaillement équivalent est fonction de la vitesse d’écoulement de la peinture pour une épaisseur particulière de peinture sur l’outil. La formulation de peinture devrait donc également avoir une viscosité élevée à des gradients de cisaillement faibles ou moyens. De plus, un pouvoir garnissant élevé de la peinture doit être recherché afin que lors de son application sur un subjectile, une quantité importante de peinture soit déposée lors de chaque passage. Un pouvoir garnissant élevé permet alors d’obtenir un feuil humide plus important lors de chaque passage de l’outil. Une viscosité élevée de la formulation de peinture doit donc être recherchée à des gradients de cisaillement élevés. Une viscosité élevée à des gradients de cisaillement élevés permettra également de réduire ou d’éliminer le risque de formation d’éclaboussures ou de gouttelettes lors de l’application de la peinture. Paint pick-up is the amount of paint carried away by means of an application tool, such as a brush, brush or roller for example. The tool immersed and then removed from the paint pot carrying a large quantity of paint will avoid having to be reloaded more frequently. Paint pick-up is an increasing function of viscosity. The equivalent shear rate calculation is a function of the paint flow rate for a particular thickness of paint on the tool. The paint formulation should therefore also have a high viscosity at low or medium shear rates. In addition, a high filling power of the paint must be sought so that when it is applied to a substrate, a large quantity of paint is deposited during each pass. A high filling power then makes it possible to obtain a greater wet film during each pass of the tool. A high viscosity of the paint formulation must therefore be sought at high shear rates. High viscosity at high shear rates will also reduce or eliminate the risk of spattering or dripping during paint application.
Une viscosité réduite à de faibles ou moyens gradients de cisaillement permettra également d’obtenir un bon aspect tendu après application de la peinture, notamment d’une peinture monocouche, sur un subjectile dont la surface revêtue présentera alors un aspect très régulier, sans bosses ni creux. L’aspect visuel final du feuil sec est alors bien meilleur.Reduced viscosity at low to medium shear rates will also provide a good taut appearance after application of paint, especially paint monolayer, on a substrate whose coated surface will then present a very regular appearance, without bumps or hollows. The final visual appearance of the dry film is then much better.
De plus, après son dépôt sur une surface, notamment une surface verticale, la peinture ne devrait pas former de coulure. Il est alors nécessaire que la formulation de peinture possède une viscosité élevée à de faibles et moyens gradients de cisaillement. In addition, after being deposited on a surface, in particular a vertical surface, the paint should not form a run. It is then necessary for the paint formulation to have a high viscosity at low and medium shear rates.
Enfin, après son dépôt sur une surface, la peinture devrait posséder une capacité de nivellement importante. Une viscosité réduite à de faibles et moyens gradients de cisaillement de la formulation de peinture est alors requise. Finally, after being deposited on a surface, the paint should have a significant leveling capacity. Reduced viscosity at low to medium shear rates of the paint formulation is then required.
Le document EP0761780 divulgue des composés diuréthanes épaississants et résistants à des hausses de température. Le document JPH06322392 décrit des additifs de dissolution pour détergent qui sont préparés à partir de diols ou de polyéthers. Le document EP0295031 divulgue un composé tensio-actif pour une résine isocyanate réticulable et préparé à partir de polyéthers. Le document US4301083 concerne la préparation de dérivés polyéthers à partir d’halogénures. Des composés de type HEUR ( hydrophobically modified ethoxylated urethanes ou uréthanes éthoxylés et modifiés de manière hydrophobe) sont connus comme agents modificateurs de rhéologie. The document EP0761780 discloses diurethane compounds that are thickening and resistant to temperature increases. JPH06322392 describes detergent dissolution additives which are prepared from diols or polyethers. Document EP0295031 discloses a surfactant compound for a crosslinkable isocyanate resin prepared from polyethers. Document US4301083 relates to the preparation of polyether derivatives from halides. Compounds of the HEUR type (hydrophobically modified ethoxylated urethanes or ethoxylated and hydrophobically modified urethanes) are known as rheology modifying agents.
Toutefois, les composés de type HEUR connus ne permettent pas toujours d’apporter de solution satisfaisante. Notamment, les composés modificateurs de rhéologie de l’état de la technique ne permettent pas toujours un contrôle efficace de la viscosité ou ne permettent pas toujours d’améliorer de manière satisfaisante le compromis entre viscosité Stormer (mesurée à faibles ou moyens gradients de cisaillement et exprimée en unité KU) et viscosité ICI (mesurée à hauts ou très hauts gradients de cisaillement et exprimée en s 1). En particulier, les composés modificateurs de rhéologie connus ne permettent pas toujours d’augmenter le rapport viscosité ICI/viscosité Stormer. However, the known HEUR-type compounds do not always make it possible to provide a satisfactory solution. In particular, the rheology modifying compounds of the state of the art do not always allow effective control of the viscosity or do not always allow the compromise between Stormer viscosity (measured at low or medium shear gradients and expressed in KU units) and ICI viscosity (measured at high or very high shear rates and expressed in s 1 ). In particular, the known rheology modifier compounds do not always make it possible to increase the ICI viscosity/Stormer viscosity ratio.
Il existe donc un besoin de disposer d’agents modificateurs de rhéologie améliorés. Le composé difonctionnel selon l’invention permet d’apporter une solution à tout ou partie des problèmes des agents modificateurs de rhéologie de l’état de la technique. There is therefore a need for improved rheology modifying agents. The difunctional compound according to the invention makes it possible to provide a solution to all or part of the problems of the rheology modifying agents of the state of the art.
Ainsi, l’invention fournit un composé difonctionnel T préparé par réaction : a. d’un équivalent molaire d’au moins un composé (a) non-alcoxylé choisi parmi :Thus, the invention provides a difunctional compound T prepared by reacting: a. a molar equivalent of at least one non-alkoxylated compound (a) chosen from:
- les composés monoisocyanates (al) aliphatiques linéaires comprenant de 6 à 40 atomes de carbone non-alcoxylés, - linear aliphatic monoisocyanate (al) compounds comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monoisocyanates (a2) aliphatiques ramifiés comprenant de 6 à 40 atomes de carbone non-alcoxylés, - les composés monoisocyanates (a3) cycloaliphatiques comprenant de 6 à 40 atomes de carbone non-alcoxylés, - branched aliphatic monoisocyanate compounds (a2) comprising from 6 to 40 non-alkoxylated carbon atoms, - cycloaliphatic monoisocyanate (a3) compounds comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monoisocyanates (a4) monoaromatiques comprenant de 6 à 30 atomes de carbone non-alcoxylés, - monoaromatic monoisocyanate compounds (a4) comprising from 6 to 30 non-alkoxylated carbon atoms,
- les composés monoisocyanates (a5) poly aromatique s comprenant de 10 à 80 atomes de carbone non-alcoxylés, - polyaromatic monoisocyanate compounds (a5) comprising from 10 to 80 non-alkoxylated carbon atoms,
- les composés monohalogénés (a6) aliphatiques linéaires comprenant de 6 à 40 atomes de carbone non-alcoxylés, - linear aliphatic monohalogen compounds (a6) comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monohalogénés (a7) aliphatiques ramifiés comprenant de 6 à 40 atomes de carbone non-alcoxylés, - branched aliphatic monohalogen compounds (a7) comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monohalogénés (a8) cycloaliphatiques comprenant de 6 à 40 atomes de carbone non-alcoxylés, - monohalogenated (a8) cycloaliphatic compounds comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monohalogénoalkylènes (a9) monoaromatiques comprenant de 7 à 30 atomes de carbone non-alcoxylés, - monoaromatic monohaloalkylene compounds (a9) comprising from 7 to 30 non-alkoxylated carbon atoms,
- les composés monohalogénoalkylènes (alO) polyaromatiques comprenant de 10 à 80 atomes de carbone non-alcoxylés, et b. d’un équivalent molaire d’au moins un composé (b) polyéthoxylé choisi parmi :- polyaromatic monohaloalkylene (alO) compounds comprising from 10 to 80 non-alkoxylated carbon atoms, and b. a molar equivalent of at least one polyethoxylated compound (b) chosen from:
- les monoalcools (bl) aliphatiques linéaires comprenant de 6 à 40 atomes de carbone polyéthoxylés comprenant strictement plus de 100 et jusqu’à 500 groupements oxyéthylène, - linear aliphatic monoalcohols (bl) comprising 6 to 40 polyethoxylated carbon atoms comprising strictly more than 100 and up to 500 oxyethylene groups,
- les monoalcools (b2) aliphatiques ramifiés comprenant de 6 à 40 atomes de carbone polyéthoxylés comprenant de 80 à 500 groupements oxyéthylène,- branched aliphatic monoalcohols (b2) comprising from 6 to 40 polyethoxylated carbon atoms comprising from 80 to 500 oxyethylene groups,
- les monoalcools (b3) cycloaliphatiques comprenant de 6 à 40 atomes de carbone polyéthoxylés comprenant de 80 à 500 groupements oxyéthylène, - cycloaliphatic monoalcohols (b3) comprising from 6 to 40 polyethoxylated carbon atoms comprising from 80 to 500 oxyethylene groups,
- les monoalcools (b4) monoaromatiques comprenant de 6 à 30 atomes de carbone polyéthoxylés comprenant strictement plus de 100 et jusqu’à 500 groupements oxyéthylène, - monoaromatic monoalcohols (b4) comprising from 6 to 30 polyethoxylated carbon atoms comprising strictly more than 100 and up to 500 oxyethylene groups,
- les monoalcools (b5) polyaromatiques comprenant de 10 à 80 atomes de carbone polyéthoxylés comprenant de 80 à 500 groupements oxyéthylène. - polyaromatic monoalcohols (b5) comprising from 10 to 80 polyethoxylated carbon atoms comprising from 80 to 500 oxyethylene groups.
De manière avantageuse selon l’invention, les composés (al) à (a5) sont issus de la réaction préalable d’un composé diisocyanate et, respectivement : Advantageously according to the invention, the compounds (al) to (a5) result from the prior reaction of a diisocyanate compound and, respectively:
- d’un monoalcool aliphatique linéaire comprenant de 6 à 40 atomes de carbone non-alcoxylé, - d’un monoalcool aliphatique ramifié comprenant de 6 à 40 atomes de carbone non-alcoxylé, - a linear aliphatic monoalcohol comprising from 6 to 40 non-alkoxylated carbon atoms, - a branched aliphatic monoalcohol comprising from 6 to 40 non-alkoxylated carbon atoms,
- d’un monoalcool cycloaliphatique comprenant de 6 à 40 atomes de carbone non-alcoxylé, - a cycloaliphatic monoalcohol comprising 6 to 40 non-alkoxylated carbon atoms,
- d’un monoalcool monoaromatique comprenant de 6 à 30 atomes de carbone non-alcoxylé, - a monoaromatic monoalcohol comprising 6 to 30 non-alkoxylated carbon atoms,
- d’un monoalcool polyaromatique comprenant de 10 à 80 atomes de carbone non-alcoxylé. - a polyaromatic monoalcohol comprising 10 to 80 non-alkoxylated carbon atoms.
Selon l’invention, les composés diisocyanates sont des composés diisocyanates symétriques ou bien des composés diisocyanates dissymétriques. Les composés diisocyanates symétriques comprennent deux groupements isocyanates qui ont la même réactivité. Les composés diisocyanates dissymétriques comprennent deux groupements isocyanates qui ont des réactivités différentes. De manière préférée selon l’invention, le composé diisocyanate est un composé dont les deux groupements isocyanates ont des réactivités différentes. Le composé diisocyanate peut être choisi parmi les composés diisocyanates dissymétriques, de préférence l’IPDI. Le composé diisocyanate peut également être le 2,6 TDI. According to the invention, the diisocyanate compounds are symmetrical diisocyanate compounds or else unsymmetrical diisocyanate compounds. Symmetrical diisocyanate compounds include two isocyanate groups that have the same reactivity. Unsymmetrical diisocyanate compounds include two isocyanate groups that have different reactivities. Preferably according to the invention, the diisocyanate compound is a compound in which the two isocyanate groups have different reactivities. The diisocyanate compound can be chosen from unsymmetrical diisocyanate compounds, preferably IPDI. The diisocyanate compound can also be 2,6 TDI.
Généralement, le composé diisocyanate peut être choisi parmi : Generally, the diisocyanate compound can be chosen from:
- certains composés diisocyanates aromatiques symétriques, de préférence : - certain symmetrical aromatic diisocyanate compounds, preferably:
• 2,2'-diisocyanate de diphénylméthylène (2,2'-MDI) et 4,4'-diisocyanate de diphénylméthylène (4,4'-MDI) ; • 2,2'-diphenylmethylene diisocyanate (2,2'-MDI) and 4,4'-diphenylmethylene diisocyanate (4,4'-MDI);
• 4,4’-dibenzyl diisocyanate (4,4’-DBDI) ; • 4,4'-dibenzyl diisocyanate (4,4'-DBDI);
• 2,6-diisocyanate de toluène (2,6-TDI) ; • 2,6-toluene diisocyanate (2,6-TDI);
• m-xylylène diisocyanate (m-XDI) ; • m-xylylene diisocyanate (m-XDI);
- certains composés diisocyanates alicycliques symétriques, de préférence méthylène bis(4-cyclohexylisocyanate) (H12MDI) ; - certain symmetrical alicyclic diisocyanate compounds, preferably methylene bis(4-cyclohexylisocyanate) (H12MDI);
- certains composés diisocyanates aliphatiques symétriques, de préférence diisocyanate d'hexaméthylène (HDI), diisocyanate de pentaméthylène (PDI) ;- certain symmetrical aliphatic diisocyanate compounds, preferably hexamethylene diisocyanate (HDI), pentamethylene diisocyanate (PDI);
- les composés diisocyanates aromatiques dissymétriques, de préférence : - unsymmetrical aromatic diisocyanate compounds, preferably:
• 2,4'-diisocyanate de diphénylméthylène (2,4'-MDI) ; • 2,4'-diisocyanate of diphenylmethylene (2,4'-MDI);
• 2,4’-dibenzyl diisocyanate (2,4’-DBDI) ; • 2,4'-dibenzyl diisocyanate (2,4'-DBDI);
• 2,4-diisocyanate de toluène (2,4-TDI) ; - les composés diisocyanates alicycliques dissymétriques, de préférence diisocyanate d'isophorone (IPDI). • 2,4-diisocyanate of toluene (2,4-TDI); - unsymmetrical alicyclic diisocyanate compounds, preferably isophorone diisocyanate (IPDI).
De manière essentielle selon l’invention, le composé difonctionnel T est préparé à partir d’au moins un composé (al) à (a5) comprenant un groupement isocyanate ou à partir d’au moins un composé (a6) à (alO) comprenant un atome d’halogène et d’un composé (b) susceptible de réagir avec ce groupement isocyanate ou avec cet atome d’halogène et comportant une chaîne hydrocarbonée - saturée, insaturée ou aromatique - combinée à une chaîne polyéthoxylée. De préférence selon l’invention, ce composé réactif (b) est un composé monohydroxylé. De manière préférée selon l’invention, la condensation des composés (al) à (a5) et du composé (b) est conduite en présence d’un catalyseur. Ce catalyseur peut être choisi parmi une amine, de préférence l,8-diazabicyclo[5.4.0]undec-7-ene (DBU), un dérivé d’un métal choisi parmi Al, Bi, Sn, Hg, Pb, Mn, Zn, Zr, Ti. Des traces d’eau peuvent également participer à la catalyse de la réaction. Comme exemples de dérivés métalliques, on préfère un dérivé choisi parmi dilaurate de dibutyl bismuth, diacétate de dibutyl bismuth, oxyde de dibutyl bismuth, carboxylate de bismuth, dilaurate de dibutyl étain, diacétate de dibutyl étain, oxyde de dibutyl étain, un dérivé du mercure, un dérivé du plomb, des sels de zinc, des sels de manganèse, un composé comprenant du zirconium chélaté, un composé comprenant de l’aluminium chélaté. Le dérivé métallique préféré est choisi parmi un dérivé de Bi, un dérivé de Sn et un dérivé de Ti. Essentially according to the invention, the difunctional compound T is prepared from at least one compound (a1) to (a5) comprising an isocyanate group or from at least one compound (a6) to (a1O) comprising a halogen atom and a compound (b) capable of reacting with this isocyanate group or with this halogen atom and comprising a hydrocarbon chain - saturated, unsaturated or aromatic - combined with a polyethoxylated chain. Preferably according to the invention, this reactive compound (b) is a monohydroxylated compound. Preferably according to the invention, the condensation of compounds (a1) to (a5) and of compound (b) is carried out in the presence of a catalyst. This catalyst can be chosen from an amine, preferably 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), a derivative of a metal chosen from Al, Bi, Sn, Hg, Pb, Mn, Zn, Zr, Ti. Traces of water can also participate in the catalysis of the reaction. As examples of metal derivatives, a derivative selected from dibutyl bismuth dilaurate, dibutyl bismuth diacetate, dibutyl bismuth oxide, bismuth carboxylate, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin oxide, a derivative of mercury is preferred. , a derivative of lead, zinc salts, manganese salts, a compound comprising chelated zirconium, a compound comprising chelated aluminium. The preferred metal derivative is selected from a Bi derivative, an Sn derivative and a Ti derivative.
De manière également préférée selon l’invention, la condensation des composés (a6) à (alO) et du composé (b) est conduite en présence d’un catalyseur, notamment une base, par exemple une base forte, telles que KOH, NaOH. Also preferably according to the invention, the condensation of the compounds (a6) to (alO) and of the compound (b) is carried out in the presence of a catalyst, in particular a base, for example a strong base, such as KOH, NaOH .
De manière préférée selon l’invention, la réaction met en œuvre un unique composé (a) ou bien la réaction met en œuvre deux ou trois composés (a) différents. Preferably according to the invention, the reaction implements a single compound (a) or else the reaction implements two or three different compounds (a).
De manière préférée selon l’invention, le composé monohalogéné est choisi parmi un composé chloré, un composé bromé, un composé iodé et leurs combinaisons, de préférence le composé monohalogéné est un composé bromé. Preferably according to the invention, the monohalogen compound is chosen from a chlorine compound, a bromine compound, an iodine compound and combinations thereof, preferably the monohalogen compound is a bromine compound.
Selon l’invention, les composés monohalogénoalkylènes (a9) monoaromatiques sont des composés comprenant un unique groupement aromatique monohalogéné par l’intermédiaire d’un groupement alkylène. L’atome d’halogène n’est pas directement porté par le groupement aromatique. Selon l’invention, les composés monohalogénoalkylènes (alO) polyaromatiques sont des composés comprenant au moins deux groupements aromatiques dont au moins un est monohalogéné par l’intermédiaire d’un groupement alkylène. L’atome d’halogène n’est pas directement porté par un groupement aromatique. De manière préférée selon l’invention, le composé (a) est tel que : According to the invention, the monoaromatic monohaloalkylene compounds (a9) are compounds comprising a single monohalogenated aromatic group via an alkylene group. The halogen atom is not directly carried by the aromatic group. According to the invention, the polyaromatic monohaloalkylene (alO) compounds are compounds comprising at least two groups aromatics, at least one of which is monohalogenated via an alkylene group. The halogen atom is not directly carried by an aromatic group. Preferably according to the invention, compound (a) is such that:
- la chaîne hydrocarbonée du composé (al) ou du composé (a6) comprend de 6 à 30 atomes de carbone, de préférence de 6 à 20 atomes de carbone ou de 8 à 16 atomes de carbone, plus préférentiellement le composé (al) ou le composé (a6) est choisi parmi n-octanyl non-alcoxylé, n-décanyl non-alcoxylé, n-dodécanyl non-alcoxylé, n-hexadécanyl non-alcoxylé, ou - the hydrocarbon chain of compound (al) or of compound (a6) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 16 carbon atoms, more preferably compound (al) or the compound (a6) is chosen from non-alkoxylated n-octanyl, non-alkoxylated n-decanyl, non-alkoxylated n-dodecanyl, non-alkoxylated n-hexadecanyl, or
- la chaîne hydrocarbonée du composé (a2) ou du composé (a7) comprend de 6 à 30 atomes de carbone, de préférence de 6 à 20 atomes de carbone ou de 8 à 16 atomes de carbone, plus préférentiellement le composé (a2) ou le composé (a7) est choisi parmi ethyl-hexanyl non-alcoxylé, iso-octanyl non-alcoxylé, iso-nonanyl non-alcoxylé, iso-décanyl non-alcoxylé, propyl-heptanyl non-alcoxylé, butyl-octanyl non-alcoxylé, iso-dodécanyl non-alcoxylé, iso-hexadécanyl non-alcoxylé, un groupement alkyl issu d’un alcool oxo non-alcoxylé, un groupement alkyl issu d’un alcool de Guerbet non-alcoxylé, ou- the hydrocarbon chain of compound (a2) or of compound (a7) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 16 carbon atoms, more preferably compound (a2) or the compound (a7) is chosen from non-alkoxylated ethyl-hexanyl, non-alkoxylated iso-octanyl, non-alkoxylated iso-nonanyl, non-alkoxylated iso-decanyl, non-alkoxylated propyl-heptanyl, non-alkoxylated butyl-octanyl, non-alkoxylated iso-dodecanyl, non-alkoxylated iso-hexadecanyl, an alkyl group derived from a non-alkoxylated oxo alcohol, an alkyl group derived from a non-alkoxylated Guerbet alcohol, or
- la chaîne hydrocarbonée du composé (a3) ou du composé (a8) comprend de 6 à 30 atomes de carbone, de préférence de 6 à 20 atomes de carbone ou de 8 à 20 atomes de carbone, plus préférentiellement le composé (a3) ou le composé (a8) est choisi parmi ethyl-cyclohexanyl non-alcoxylé, n-nonyl-cyclohexanyl non-alcoxylé, n-dodécyl-cyclohexanyl non-alcoxylé, ou - the hydrocarbon chain of compound (a3) or of compound (a8) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 20 carbon atoms, more preferably compound (a3) or the compound (a8) is chosen from non-alkoxylated ethyl-cyclohexanyl, non-alkoxylated n-nonyl-cyclohexanyl, non-alkoxylated n-dodecyl-cyclohexanyl, or
- la chaîne hydrocarbonée du composé (a4) ou du composé (a9) comprend de 12 à 30 atomes de carbone ou de 12 à 22 atomes de carbone, de préférence le composé (a4) ou le composé (a9) est choisi parmi n-pentadocécyl-phényl non-alcoxylé ou- the hydrocarbon chain of compound (a4) or of compound (a9) comprises from 12 to 30 carbon atoms or from 12 to 22 carbon atoms, preferably compound (a4) or compound (a9) is chosen from n- non-alkoxylated pentadocecyl-phenyl or
- la chaîne hydrocarbonée du composé (a5) ou du composé (alO) comprend de 10 à 60 atomes de carbone, de préférence le composé (a5) ou le composé (alO) est choisi parmi naphtyl non-alcoxylé, distyryl-phényl non-alcoxylé, tristyryl-phényl non-alcoxylé, pentastyryl-cumyl-phényl non-alcoxylé. - the hydrocarbon chain of the compound (a5) or of the compound (alO) comprises from 10 to 60 carbon atoms, preferably the compound (a5) or the compound (alO) is chosen from non-alkoxylated naphthyl, non-alkoxylated distyryl-phenyl alkoxylated, non-alkoxylated tristyryl-phenyl, non-alkoxylated pentastyryl-cumyl-phenyl.
Selon l’invention, les monoalcools sont des composés comprenant un seul groupement hydroxyle (OH) qui est terminal. Selon l’invention, les monoalcools polyéthoxylés sont des composés comprenant une chaîne hydrocarbonée qui comprend plusieurs groupements oxyéthylène et un groupement hydroxyle (OH) terminal. Selon l’invention, les monoalcools polyéthoxylés sont des composés de formule R-(LO)n-H dans laquelle R représente une chaîne hydrocarbonée, n représente le nombre de polyaéthoxylations et L, identique ou différent, représente indépendamment un groupement alkylène linéaire comprenant 2 atomes de carbone. Selon l’invention, les monoalcools non-alcoxylés sont des composés comprenant une chaîne hydrocarbonée et un seul groupement hydroxyle (OH) terminal. Selon l’invention, les monoalcools non-alcoxylés sont des composés de formule R’ -OH dans laquelle R’ représente une chaîne hydrocarbonée. Selon l’invention, le nombre d’atomes de carbones définissant les monoalcools (bl) à (b5) correspond donc au nombre d’atomes de carbones des groupements R ou R’. According to the invention, monoalcohols are compounds comprising a single hydroxyl group (OH) which is terminal. According to the invention, the polyethoxylated monoalcohols are compounds comprising a hydrocarbon chain which comprises several oxyethylene groups and a terminal hydroxyl (OH) group. According to the invention, the polyethoxylated monoalcohols are compounds of formula R-(LO) n -H in which R represents a hydrocarbon chain, n represents the number of polyethoxylations and L, identical or different, independently represents a linear alkylene group comprising 2 carbon atoms. According to the invention, the non-alkoxylated monoalcohols are compounds comprising a hydrocarbon chain and a single terminal hydroxyl (OH) group. According to the invention, the non-alkoxylated monoalcohols are compounds of formula R'-OH in which R' represents a hydrocarbon chain. According to the invention, the number of carbon atoms defining the monoalcohols (b1) to (b5) therefore corresponds to the number of carbon atoms of the groups R or R′.
De manière préférée selon l’invention, les monoalcools polyéthoxylés (bl) et (b3) comprennent de 105 à 400 groupements éthoxylés ou de 105 à 200 groupements éthoxylés. De manière préférée selon l’invention, les monoalcools polyéthoxylés (b2), (b4) et (b5) comprennent de 80 à 400 groupements éthoxylés ou de 100 à 200 groupements éthoxylés. Selon l’invention, les composés (b) polyéthoxylés mis en œuvre peuvent comprendre un nombre de groupements éthoxylés identiques ou différents. Selon l’invention, les groupements éthoxylés sont des groupements oxyéthylène (-CH2CH2O-). De manière essentielle selon l’invention, le composé T est un composé comprenant des groupements éthoxylés. Préférentiellement selon l’invention, le composé T a un degré de polyéthoxylation compris entre 100 et 500 ou entre 100 et 502. Le degré de polyéthoxylation définit le nombre de groupements éthoxylés compris dans ce composé. De manière préférée selon l’invention, le composé (b) est tel que : - la chaîne hydrocarbonée du composé (bl) comprend de 6 à 30 atomes de carbone, de préférence de 6 à 20 atomes de carbone ou de 8 à 16 atomes de carbone, plus préférentiellement le composé (bl) est choisi parmi n-octanol polyéthoxylé, n-décanol polyéthoxylé, n-dodécanol polyéthoxylé, n-hexadécanol polyéthoxylé, ou - la chaîne hydrocarbonée du composé (b2) comprend de 6 à 30 atomes de carbone, de préférence de 6 à 20 atomes de carbone ou de 8 à 16 atomes de carbone, plus préférentiellement le composé (b2) est choisi parmi ethyl-hexanol polyéthoxylé, iso-octanol polyéthoxylé, iso-nonanol polyéthoxylé, iso-décanol polyéthoxylé, propyl-heptanol polyéthoxylé, butyl-octanol polyéthoxylé, iso-dodécanol polyéthoxylé, iso-hexadécanol polyéthoxylé, un alcool oxo polyéthoxylé, un alcool de Guerbet polyéthoxylé, ou Preferably according to the invention, the polyethoxylated monoalcohols (b1) and (b3) comprise from 105 to 400 ethoxylated groups or from 105 to 200 ethoxylated groups. Preferably according to the invention, the polyethoxylated monoalcohols (b2), (b4) and (b5) comprise from 80 to 400 ethoxylated groups or from 100 to 200 ethoxylated groups. According to the invention, the polyethoxylated compounds (b) used may comprise a number of identical or different ethoxylated groups. According to the invention, the ethoxylated groups are oxyethylene groups (-CH2CH2O-). Essentially according to the invention, compound T is a compound comprising ethoxylated groups. Preferably according to the invention, compound T has a degree of polyethoxylation of between 100 and 500 or between 100 and 502. The degree of polyethoxylation defines the number of ethoxylated groups included in this compound. Preferably according to the invention, compound (b) is such that: - the hydrocarbon chain of compound (bl) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 16 carbon, more preferably the compound (bl) is chosen from polyethoxylated n-octanol, polyethoxylated n-decanol, polyethoxylated n-dodecanol, polyethoxylated n-hexadecanol, or - the hydrocarbon chain of the compound (b2) comprises from 6 to 30 atoms of carbon, preferably from 6 to 20 carbon atoms or from 8 to 16 carbon atoms, more preferably compound (b2) is chosen from polyethoxylated ethyl-hexanol, polyethoxylated iso-octanol, polyethoxylated iso-nonanol, polyethoxylated iso-decanol, polyethoxylated propyl-heptanol, polyethoxylated butyl-octanol, polyethoxylated iso-dodecanol, polyethoxylated iso-hexadecanol, a polyethoxylated oxo alcohol, a polyethoxylated Guerbet alcohol, or
- la chaîne hydrocarbonée du composé (b3) comprend de 6 à 30 atomes de carbone, de préférence de 6 à 20 atomes de carbone ou de 8 à 20 atomes de carbone, plus préférentiellement le composé (b3) est choisi parmi ethyl-cyclohexanol polyéthoxylé, n-nonyl-cyclohexanol polyéthoxylé, n-dodécyl-cyclohexanol polyéthoxylé, ou - the hydrocarbon chain of compound (b3) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 20 carbon atoms, more preferably compound (b3) is chosen from ethyl-cyclohexanol polyethoxylated, polyethoxylated n-nonyl-cyclohexanol, polyethoxylated n-dodecyl-cyclohexanol, or
- la chaîne hydrocarbonée du composé (b4) comprend de 12 à 30 atomes de carbone ou de 12 à 22 atomes de carbone, de préférence le composé (b4) est choisi parmi n-pentadocécyl-phénol polyéthoxylé ou - the hydrocarbon chain of compound (b4) comprises from 12 to 30 carbon atoms or from 12 to 22 carbon atoms, preferably compound (b4) is chosen from polyethoxylated n-pentadocecyl-phenol or
- la chaîne hydrocarbonée du composé (b5) comprend de 10 à 60 atomes de carbone, de préférence le composé (b5) est choisi parmi naphtol polyéthoxylé, distyryl-phénol polyéthoxylé, tristyryl-phénol polyéthoxylé, pentastyryl-cumyl-phénol polyéthoxylé. - the hydrocarbon chain of compound (b5) comprises from 10 to 60 carbon atoms, preferably compound (b5) is chosen from polyethoxylated naphthol, polyethoxylated distyryl-phenol, polyethoxylated tristyryl-phenol, polyethoxylated pentastyryl-cumyl-phenol.
De manière essentielle selon l’invention, le composé T est préparé au moyen d’un monoalcool et en l’absence de diol ou de triol ou en l’absence de composé comprenant au moins deux groupements hydroxyles (OH). Essentially according to the invention, the compound T is prepared by means of a monoalcohol and in the absence of diol or triol or in the absence of a compound comprising at least two hydroxyl groups (OH).
Outre un composé difonctionnel T, l’invention concerne également une méthode de préparation de ce composé. In addition to a difunctional compound T, the invention also relates to a method for preparing this compound.
Ainsi, l’invention fournit une méthode de préparation d’un composé difonctionnel T par réaction : a. d’un équivalent molaire d’au moins un composé (a) non-alcoxylé choisi parmi :Thus, the invention provides a method for preparing a difunctional compound T by reaction: a. a molar equivalent of at least one non-alkoxylated compound (a) chosen from:
- les composés monoisocyanates (al) aliphatiques linéaires comprenant de 6 à 40 atomes de carbone non-alcoxylés, - linear aliphatic monoisocyanate (al) compounds comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monoisocyanates (a2) aliphatiques ramifiés comprenant de 6 à 40 atomes de carbone non-alcoxylés, - branched aliphatic monoisocyanate compounds (a2) comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monoisocyanates (a3) cycloaliphatiques comprenant de 6 à 40 atomes de carbone non-alcoxylés, - cycloaliphatic monoisocyanate (a3) compounds comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monoisocyanates (a4) monoaromatiques comprenant de 6 à 30 atomes de carbone non-alcoxylés, - monoaromatic monoisocyanate compounds (a4) comprising from 6 to 30 non-alkoxylated carbon atoms,
- les composés monoisocyanates (a5) polyaromatiques comprenant de 10 à 80 atomes de carbone non-alcoxylés, - polyaromatic monoisocyanate compounds (a5) comprising from 10 to 80 non-alkoxylated carbon atoms,
- les composés monohalogénés (a6) aliphatiques linéaires comprenant de 6 à 40 atomes de carbone non-alcoxylés, - linear aliphatic monohalogen compounds (a6) comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monohalogénés (a7) aliphatiques ramifiés comprenant de 6 à 40 atomes de carbone non-alcoxylés, - branched aliphatic monohalogen compounds (a7) comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monohalogénés (a8) cycloaliphatiques comprenant de 6 à 40 atomes de carbone non-alcoxylés, - les composés monohalogénoalkylènes (a9) monoaromatiques comprenant de 7 à 30 atomes de carbone non-alcoxylés, - monohalogenated (a8) cycloaliphatic compounds comprising from 6 to 40 non-alkoxylated carbon atoms, - monoaromatic monohaloalkylene compounds (a9) comprising from 7 to 30 non-alkoxylated carbon atoms,
- les composés monohalogénoalkylènes (alO) polyaromatiques comprenant de 10 à 80 atomes de carbone non-alcoxylés, et b. d’un équivalent molaire d’au moins un composé (b) polyéthoxylé choisi parmi :- polyaromatic monohaloalkylene (alO) compounds comprising from 10 to 80 non-alkoxylated carbon atoms, and b. a molar equivalent of at least one polyethoxylated compound (b) chosen from:
- les monoalcools (bl) aliphatiques linéaires comprenant de 6 à 40 atomes de carbone polyéthoxylés comprenant strictement plus de 100 et jusqu’à 500 groupements oxyéthylène, - linear aliphatic monoalcohols (bl) comprising 6 to 40 polyethoxylated carbon atoms comprising strictly more than 100 and up to 500 oxyethylene groups,
- les monoalcools (b2) aliphatiques ramifiés comprenant de 6 à 40 atomes de carbone polyéthoxylés comprenant de 80 à 500 groupements oxyéthylène,- branched aliphatic monoalcohols (b2) comprising from 6 to 40 polyethoxylated carbon atoms comprising from 80 to 500 oxyethylene groups,
- les monoalcools (b3) cycloaliphatiques comprenant de 6 à 40 atomes de carbone polyéthoxylés comprenant de 80 à 500 groupements oxyéthylène, - cycloaliphatic monoalcohols (b3) comprising from 6 to 40 polyethoxylated carbon atoms comprising from 80 to 500 oxyethylene groups,
- les monoalcools (b4) monoaromatiques comprenant de 6 à 30 atomes de carbone polyéthoxylés comprenant strictement plus de 100 et jusqu’à 500 groupements oxyéthylène, - monoaromatic monoalcohols (b4) comprising from 6 to 30 polyethoxylated carbon atoms comprising strictly more than 100 and up to 500 oxyethylene groups,
- les monoalcools (b5) polyaromatiques comprenant de 10 à 80 atomes de carbone polyéthoxylés comprenant de 80 à 500 groupements oxyéthylène. - polyaromatic monoalcohols (b5) comprising from 10 to 80 polyethoxylated carbon atoms comprising from 80 to 500 oxyethylene groups.
De manière préférée selon l’invention pour la méthode de préparation selon l’invention, la condensation des composés (al) à (a5) et (b) est conduite en présence d’un catalyseur. De manière plus préférée, la réaction est catalysée au moyen d’une amine, de préférence au moyen de l,8-diazabicyclo[5.4.0]undec-7-ene (DBU), ou d’au moins un dérivé d’un métal choisi parmi Al, Bi, Sn, Hg, Pb, Mn, Zn, Zr, Ti. Des traces d’eau peuvent également participer à la catalyse de la réaction. Comme exemples de dérivés métalliques, on préfère un dérivé choisi parmi le dilaurate de dibutyl bismuth, diacétate de dibutyl bismuth, oxyde de dibutyl bismuth, carboxylate de bismuth, dilaurate de dibutyl étain, diacétate de dibutyl étain, oxyde de dibutyl étain, un dérivé du mercure, un dérivé du plomb, des sels de zinc, des sels de manganèse, un composé comprenant du zirconium chélaté, un composé comprenant de l’aluminium chélaté. Le dérivé métallique préféré est choisi parmi un dérivé de Bi, un dérivé de Sn et un dérivé de Ti. Preferably according to the invention for the method of preparation according to the invention, the condensation of the compounds (al) to (a5) and (b) is carried out in the presence of a catalyst. More preferably, the reaction is catalyzed by means of an amine, preferably by means of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), or at least one derivative of a metal chosen from Al, Bi, Sn, Hg, Pb, Mn, Zn, Zr, Ti. Traces of water can also participate in the catalysis of the reaction. As examples of metal derivatives, a derivative selected from dibutyl bismuth dilaurate, dibutyl bismuth diacetate, dibutyl bismuth oxide, bismuth carboxylate, dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin oxide, a derivative of mercury, a derivative of lead, zinc salts, manganese salts, a compound comprising chelated zirconium, a compound comprising chelated aluminium. The preferred metal derivative is selected from a Bi derivative, an Sn derivative and a Ti derivative.
De manière également préférée selon l’invention, la condensation des composés (a6) à (alO) et du composé (b) est conduite en présence d’un catalyseur, notamment une base, par exemple une base forte, telles que KOH, NaOH. Also preferably according to the invention, the condensation of the compounds (a6) to (alO) and of the compound (b) is carried out in the presence of a catalyst, in particular a base, for example a strong base, such as KOH, NaOH .
De manière avantageuse selon l’invention, la condensation des composés (a) et (b) est conduite dans un solvant organique. Les solvants organiques préférés sont des solvants non-réactifs avec les fonctions isocyanates ou avec les atomes d’halogène du composé (a), en particulier les solvants choisis parmi les solvants hydrocarbonés (notamment des coupes pétrolières en Cs à C30), les solvants aromatiques (notamment toluène et ses dérivés) et leurs combinaisons. De manière plus préférée selon l’invention, la condensation est conduite directement avec les différents réactifs ou bien est conduite dans le toluène.Advantageously according to the invention, the condensation of compounds (a) and (b) is carried out in an organic solvent. Preferred organic solvents are solvents non-reactive with the isocyanate functions or with the halogen atoms of compound (a), in particular the solvents chosen from hydrocarbon solvents (in particular Cs to C30 petroleum fractions), aromatic solvents (in particular toluene and its derivatives) and their combinations. More preferably according to the invention, the condensation is carried out directly with the various reagents or else is carried out in toluene.
À l’issue de la préparation du composé T selon l’invention, on obtient une solution du composé dans un solvant organique. Une telle solution peut être mise en œuvre directement. Également selon l’invention, le solvant organique peut être séparé et le composé T séché. Un tel composé T selon l’invention, qui est séché, peut alors être mis en œuvre sous forme solide, par exemple sous forme de poudre ou de granulés. At the end of the preparation of compound T according to the invention, a solution of the compound is obtained in an organic solvent. Such a solution can be implemented directly. Also according to the invention, the organic solvent can be separated and the compound T dried. Such a compound T according to the invention, which is dried, can then be implemented in solid form, for example in the form of powder or granules.
Outre le composé difonctionnel T et une méthode de préparation de ce composé, l’invention concerne également une composition aqueuse comprenant au moins un composé difonctionnel T selon l’invention. L’invention concerne également une composition aqueuse comprenant au moins un composé difonctionnel T préparé selon la méthode de préparation selon l’invention. In addition to the difunctional compound T and a method for preparing this compound, the invention also relates to an aqueous composition comprising at least one difunctional compound T according to the invention. The invention also relates to an aqueous composition comprising at least one difunctional compound T prepared according to the preparation method according to the invention.
De manière avantageuse, le composé difonctionnel selon l’invention est un composé possédant un caractère hydrophile. Il peut être formulé en milieu aqueux. Advantageously, the difunctional compound according to the invention is a compound having a hydrophilic character. It can be formulated in an aqueous medium.
La composition aqueuse selon l’invention peut également comprendre au moins un additif, en particulier un additif choisi parmi : The aqueous composition according to the invention may also comprise at least one additive, in particular an additive chosen from:
- un composé amphiphile, notamment un composé tensio-actif, de préférence un composé tensio-actif hydroxylé, par exemple alkyl-polyalkyleneglycol, notamment alkyl-polyethyleneglycol et alkyl-polypropyleneglycol ; - an amphiphilic compound, in particular a surfactant compound, preferably a hydroxylated surfactant compound, for example alkyl-polyalkylene glycol, in particular alkyl-polyethylene glycol and alkyl-polypropylene glycol;
- un dérivé de polysaccharide, par exemple cyclodextrine, dérivé de cyclodextrine, polyéthers, alkyl-glucosides ; - a polysaccharide derivative, for example cyclodextrin, cyclodextrin derivative, polyethers, alkyl-glucosides;
- solvants, notamment solvants de coalescence, et composés hydrotropes, par exemple glycol, butylglycol, butyldiglycol, monopropyleneglycol, ethyleneglycol, ethylenediglycol, produits Dowanol dont le numéro CAS est 34590-94-8), produits Texanol dont le numéro CAS est 25265-77-4) ; - solvents, in particular coalescence solvents, and hydrotropic compounds, for example glycol, butylglycol, butyldiglycol, monopropyleneglycol, ethyleneglycol, ethylenediglycol, Dowanol products whose CAS number is 34590-94-8), Texanol products whose CAS number is 25265-77 -4);
- agents anti-mousse, agents biocides. - anti-foaming agents, biocidal agents.
L’invention fournit également une formulation aqueuse qui peut être utilisée dans de nombreux domaines techniques. La formulation aqueuse selon l’invention comprend au moins une composition selon l’invention et peut comprendre au moins un pigment organique ou minéral ou des particules organiques, organo-métalliques ou minérales, par exemple carbonate de calcium, talc, kaolin, mica, silicates, silice, oxydes métalliques, notamment dioxyde de titane, oxydes de fer. La formulation aqueuse selon l’invention peut également comprendre au moins un agent choisi parmi un agent espaceur de particules, un agent dispersant, un agent stabilisant stérique, un agent stabilisant électrostatique, un agent opacifiant, un solvant, un agent de coalescence, un agent anti-mousse, un agent de conservation, un agent biocide, un agent d’étalement, un agent épaississant, un copolymère filmogène et leurs mélanges. The invention also provides an aqueous formulation which can be used in many technical fields. The aqueous formulation according to the invention comprises at least one composition according to the invention and may comprise at least one organic or inorganic pigment or organic, organo-metallic or inorganic particles, for example calcium carbonate, talc, kaolin, mica, silicates , silica, metal oxides, including titanium dioxide, iron oxides. The aqueous formulation according to the invention may also comprise at least one agent chosen from a particle spacer, a dispersing agent, a steric stabilizing agent, an electrostatic stabilizing agent, an opacifying agent, a solvent, a coalescing agent, a antifoam, a preservative, a biocidal agent, a spreading agent, a thickening agent, a film-forming copolymer and mixtures thereof.
Selon le composé difonctionnel particulier ou les additifs qu’elle comprend la formulation selon l’invention peut être mise en œuvre dans de nombreux domaines techniques. Ainsi, la formulation selon l’invention peut être une formulation de revêtement. De préférence, la formulation selon l’invention est une formulation d’encre, une formulation d’adhésif, une formulation de vernis, une formulation de peinture, par exemple de peinture décorative ou de peinture industrielle. De préférence, la formulation selon l’invention est une formulation de peinture. Depending on the particular difunctional compound or the additives that it comprises, the formulation according to the invention can be implemented in numerous technical fields. Thus, the formulation according to the invention can be a coating formulation. Preferably, the formulation according to the invention is an ink formulation, an adhesive formulation, a varnish formulation, a paint formulation, for example decorative paint or industrial paint. Preferably, the formulation according to the invention is a paint formulation.
L’invention fournit également une pâte pigmentaire aqueuse concentrée comprenant au moins un composé difonctionnel T selon l’invention ou au moins un composé difonctionnel T préparé selon la méthode de préparation selon l’invention et au moins un pigment coloré organique ou minéral. The invention also provides a concentrated aqueous pigment paste comprising at least one difunctional compound T according to the invention or at least one difunctional compound T prepared according to the preparation method according to the invention and at least one organic or inorganic colored pigment.
Le composé difonctionnel selon l’invention possède des propriétés permettant de l’utiliser pour modifier ou contrôler la rhéologie du milieu le comprenant. Ainsi, l’invention fournit également une méthode de contrôle de la viscosité d’une composition aqueuse. The difunctional compound according to the invention has properties allowing it to be used to modify or control the rheology of the medium comprising it. Thus, the invention also provides a method for controlling the viscosity of an aqueous composition.
Cette méthode de contrôle de la viscosité selon l’invention comprend l’addition d’au moins un composé difonctionnel T selon l’invention dans une composition aqueuse. Cette méthode de contrôle de la viscosité peut également comprendre l’addition d’au moins un composé difonctionnel T préparé selon la méthode de préparation selon l’invention. De manière préférée, la méthode de contrôle de la viscosité selon l’invention est mise en œuvre au moyen d’une composition aqueuse selon l’invention. De manière également préférée, la méthode de contrôle de la viscosité selon l’invention est mise en œuvre au moyen d’une formulation aqueuse selon l’invention. This viscosity control method according to the invention comprises the addition of at least one difunctional compound T according to the invention in an aqueous composition. This viscosity control method can also comprise the addition of at least one difunctional compound T prepared according to the preparation method according to the invention. Preferably, the viscosity control method according to the invention is implemented by means of an aqueous composition according to the invention. Also preferably, the method for controlling the viscosity according to the invention is implemented by means of an aqueous formulation according to the invention.
Les caractéristiques préférées, particulières ou avantageuses du composé difonctionnel T selon l’invention définissent des compositions aqueuses selon l’invention, des formulations selon l’invention, des pâtes pigmentaires et des méthodes de contrôle de la viscosité qui sont également préférées, particulières ou avantageuses. The preferred, particular or advantageous characteristics of the difunctional compound T according to the invention define aqueous compositions according to the invention, formulations according to the invention, pigment pastes and viscosity control methods which are also preferred, particular or advantageous. .
Les exemples qui suivent permettent d’illustrer les différents aspects de l’invention. EXEMPLES The examples which follow make it possible to illustrate the various aspects of the invention. EXAMPLES
Exemple 1 : préparation de composés difonctionnels selon l’invention Example 1: preparation of difunctional compounds according to the invention
Exemple 1-1 : préparation d’un composé Tl selon l’invention Example 1-1: preparation of a compound T1 according to the invention
Dans un réacteur en verre de 3 L (récipient 1) équipé d’une agitation mécanique, d’une pompe à vide, d’une entrée d’azote et chauffé au moyen d’une double enveloppe dans laquelle circule de l’huile, on introduit 450,60 g de dodécanol éthoxylé avec 140 moles d’oxyde d’éthylène (MM = 6 355Da) que l’on chauffe à 90°C sous atmosphère inerte. Ce produit est déshydraté. In a 3 L glass reactor (receptacle 1) equipped with mechanical stirring, a vacuum pump, a nitrogen inlet and heated by means of a double jacket in which oil circulates, 450.60 g of ethoxylated dodecanol are introduced with 140 moles of ethylene oxide (MM=6355 Da) which is heated to 90° C. under an inert atmosphere. This product is dehydrated.
Parallèlement, dans un ballon tricol en verre de 100 mL (récipient 2), on introduit 15,76 g d’IPDI auxquels on ajoute 400 ppm de catalyseur carboxylate de bismuth. On purge le milieu à l’azote puis on le chauffe jusqu’à 50°C. Lorsque cette température est atteinte, on introduit progressivement 9,23 g d’octanol. At the same time, 15.76 g of IPDI are introduced into a 100 mL three-necked glass flask (receptacle 2), to which 400 ppm of bismuth carboxylate catalyst are added. The medium is purged with nitrogen and then heated to 50°C. When this temperature is reached, 9.23 g of octanol are gradually introduced.
Après addition complète, le mélange réactionnel est laissé sous agitation pendant 15 minutes. Puis, on vérifie que le taux théorique de fonctions NCO est atteint par un dosage en retour. On prélève 1 g du milieu réactionnel auquel on ajoute un excès de dibutylamine (1 molaire par exemple) qui réagit avec les fonctions isocyanates présentes dans le milieu. La dibutylamine n'ayant pas réagi est ensuite dosée avec de l’acide chlorhydrique (1 N par exemple). On peut alors en déduire la quantité de fonctions isocyanates présentes dans le milieu réactionnel. Puis, on coule le contenu du récipient 2 dans le récipient 1. On maintient l’agitation pendant 60 minutes à 90 ± 1°C. On vérifie que le taux de fonction NCO est nul indiquant la fin de la réaction. Si celui-ci est non nul, la réaction est prolongée par période de 15 minutes jusqu’à achèvement de la réaction. Lorsque le taux atteint zéro, le composé Tl obtenu est formulé dans l’eau avec adjonction de 1 000 ppm d’un agent biocide (Biopol SMV Chemipol) et de 1 000 ppm d’un agent anti-mousse (Tego 1488 Evonik). On obtient une composition 1 constituée de 20 % en masse de composé Tl selon l’invention et de 80 % en masse d’eau. After complete addition, the reaction mixture is left under stirring for 15 minutes. Then, it is verified that the theoretical rate of NCO functions is reached by a return dosing. 1 g of the reaction medium is taken, to which an excess of dibutylamine (1 molar for example) is added, which reacts with the isocyanate functions present in the medium. The unreacted dibutylamine is then dosed with hydrochloric acid (1 N for example). The quantity of isocyanate functions present in the reaction medium can then be deduced therefrom. Then, the contents of container 2 are poured into container 1. Stirring is maintained for 60 minutes at 90 ± 1°C. It is checked that the level of NCO function is zero indicating the end of the reaction. If this is non-zero, the reaction is prolonged for periods of 15 minutes until the reaction is complete. When the level reaches zero, the compound T1 obtained is formulated in water with the addition of 1,000 ppm of a biocidal agent (Biopol SMV Chemipol) and 1,000 ppm of an anti-foaming agent (Tego 1488 Evonik). A composition 1 consisting of 20% by mass of compound T1 according to the invention and 80% by mass of water is obtained.
Exemple 1-2 : préparation d’un composé T2 selon l’invention Dans un réacteur en verre de 3 L (récipient 1) équipé d’une agitation mécanique, d’une pompe à vide, d’une entrée d’azote et chauffé au moyen d’une double enveloppe dans laquelle circule de l’huile, on introduit 448,10 g de dodécanol éthoxylé avec 140 moles d’oxyde d’éthylène (MM = 6 355Da) que Ton chauffe à 90°C sous atmosphère inerte. Ce produit est déshydraté. Parallèlement, dans un ballon tricol en verre de 100 mL (récipient 2), on introduit 15,67 g d’IPDI auxquels on ajoute 400 ppm de catalyseur carboxylate de bismuth. On purge le milieu à l’azote puis on le chauffe jusqu’à 50°C. Lorsque cette température est atteinte, on introduit progressivement 11,16 g de décanol. Après addition complète, le mélange réactionnel est laissé sous agitation pendant 15 minutes. Puis, on vérifie que le taux théorique de fonctions NCO est atteint par un dosage en retour. Example 1-2: preparation of a compound T2 according to the invention In a 3 L glass reactor (receptacle 1) equipped with mechanical stirring, a vacuum pump, a nitrogen inlet and heated 448.10 g of dodecanol ethoxylated with 140 moles of ethylene oxide (MM=6355Da) are introduced by means of a jacket in which oil circulates, which is heated to 90° C. under an inert atmosphere. This product is dehydrated. At the same time, 15.67 g of IPDI are introduced into a 100 mL three-necked glass flask (receptacle 2), to which 400 ppm of bismuth carboxylate catalyst are added. The medium is purged with nitrogen and then heated to 50°C. When this temperature is reached, 11.16 g of decanol are gradually introduced. After complete addition, the reaction mixture is left under stirring for 15 minutes. Then, it is verified that the theoretical rate of NCO functions is reached by a return dosing.
Puis, on coule le contenu du récipient 2 dans le récipient 1. On maintient l’agitation pendant 60 minutes à 90 ± 1°C. On vérifie que le taux de fonction NCO est nul indiquant la fin de la réaction. Si celui-ci est non nul, la réaction est prolongée par période de 15 minutes jusqu’à achèvement de la réaction. Lorsque le taux atteint zéro, le composé T2 obtenu est formulé dans l’eau avec adjonction de 1 000 ppm d’un agent biocide (Biopol SMV Chemipol) et de 1 000 ppm d’un agent anti-mousse (Tego 1488 Evonik). On obtient une composition 2 constituée de 20 % en masse de composé T2 selon l’invention et de 80 % en masse d’eau. Then, the contents of container 2 are poured into container 1. Stirring is maintained for 60 minutes at 90 ± 1°C. It is checked that the NCO function level is zero indicating the end of the reaction. If this is non-zero, the reaction is prolonged for periods of 15 minutes until the reaction is complete. When the rate reaches zero, the compound T2 obtained is formulated in water with the addition of 1,000 ppm of a biocidal agent (Biopol SMV Chemipol) and 1,000 ppm of an anti-foaming agent (Tego 1488 Evonik). A composition 2 is obtained consisting of 20% by mass of compound T2 according to the invention and 80% by mass of water.
Exemple 1-3 : préparation d’un composé T3 selon l’invention Example 1-3: preparation of a compound T3 according to the invention
Dans un réacteur en verre de 3 L (récipient 1) équipé d’une agitation mécanique, d’une pompe à vide, d’une entrée d’azote et chauffé au moyen d’une double enveloppe dans laquelle circule de l’huile, on introduit 453,00 g de dodécanol éthoxylé avec 140 moles d’oxyde d’éthylène (MM = 6 355Da) que l’on chauffe à 90°C sous atmosphère inerte. Ce produit est déshydraté. In a 3 L glass reactor (receptacle 1) equipped with mechanical stirring, a vacuum pump, a nitrogen inlet and heated by means of a double jacket in which oil circulates, 453.00 g of dodecanol ethoxylated with 140 moles of ethylene oxide (MM=6355 Da) are introduced, which is heated to 90° C. under an inert atmosphere. This product is dehydrated.
Parallèlement, dans un ballon tricol en verre de 100 mL (récipient 2), on introduit 15,85 g d’IPDI auxquels on ajoute 400 ppm de catalyseur carboxylate de bismuth. On purge le milieu à l’azote puis on le chauffe jusqu’à 50°C. Lorsque cette température est atteinte, on introduit progressivement 13,28 g de dodécanol. At the same time, 15.85 g of IPDI are introduced into a 100 mL three-necked glass flask (receptacle 2), to which 400 ppm of bismuth carboxylate catalyst are added. The medium is purged with nitrogen and then heated to 50°C. When this temperature is reached, 13.28 g of dodecanol are gradually introduced.
Après addition complète, le mélange réactionnel est laissé sous agitation pendant 15 minutes. Puis, on vérifie que le taux théorique de fonctions NCO est atteint par un dosage en retour. Puis, on coule le contenu du récipient 2 dans le récipient 1. On maintient l’agitation pendant 60 minutes à 90 ± 1°C. On vérifie que le taux de fonction NCO est nul indiquant la fin de la réaction. Si celui-ci est non nul, la réaction est prolongée par période de 15 minutes jusqu’à achèvement de la réaction. Lorsque le taux atteint zéro, le composé T3 obtenu est formulé dans l’eau avec adjonction de 1 000 ppm d’un agent biocide (Biopol SMV Chemipol) et de 1 000 ppm d’un agent anti-mousse (Tego 1488 Evonik). On obtient une composition 3 constituée de 20 % en masse de composé T3 selon l’invention et de 80 % en masse d’eau. Exemple 1-4 : préparation d’un composé T4 selon l’invention After complete addition, the reaction mixture is left under stirring for 15 minutes. Then, it is verified that the theoretical rate of NCO functions is reached by a return dosing. Then, the contents of container 2 are poured into container 1. Stirring is maintained for 60 minutes at 90±1°C. It is checked that the NCO function level is zero indicating the end of the reaction. If the latter is non-zero, the reaction is prolonged for periods of 15 minutes until the reaction is complete. When the level reaches zero, the compound T3 obtained is formulated in water with the addition of 1,000 ppm of a biocidal agent (Biopol SMV Chemipol) and 1000 ppm of an anti-foaming agent (Tego 1488 Evonik). A composition 3 consisting of 20% by mass of compound T3 according to the invention and 80% by mass of water is obtained. Example 1-4: preparation of a compound T4 according to the invention
Dans un réacteur en verre de 3 L (récipient 1) équipé d’une agitation mécanique, d’une pompe à vide, d’une entrée d’azote et chauffé au moyen d’une double enveloppe dans laquelle circule de l’huile, on introduit 449,80 g de dodécanol éthoxylé avec 140 moles d’oxyde d’éthylène (MM = 6 355Da) que l’on chauffe à 90°C sous atmosphère inerte. Ce produit est déshydraté. In a 3 L glass reactor (receptacle 1) equipped with mechanical stirring, a vacuum pump, a nitrogen inlet and heated by means of a double jacket in which oil circulates, 449.80 g of ethoxylated dodecanol are introduced with 140 moles of ethylene oxide (MM=6355 Da) which is heated to 90° C. under an inert atmosphere. This product is dehydrated.
Parallèlement, dans un ballon tricol en verre de 100 mL (récipient 2), on introduit 15,73 g d’IPDI auxquels on ajoute 400 ppm de catalyseur carboxylate de bismuth. On purge le milieu à l’azote puis on le chauffe jusqu’à 50°C. Lorsque cette température est atteinte, on introduit progressivement 17,16 g d’hexadécanol. Après addition complète, le mélange réactionnel est laissé sous agitation pendant 15 minutes. Puis, on vérifie que le taux théorique de fonctions NCO est atteint par un dosage en retour. At the same time, 15.73 g of IPDI are introduced into a 100 mL three-necked glass flask (receptacle 2), to which 400 ppm of bismuth carboxylate catalyst are added. The medium is purged with nitrogen and then heated to 50°C. When this temperature is reached, 17.16 g of hexadecanol are gradually introduced. After complete addition, the reaction mixture is left under stirring for 15 minutes. Then, it is verified that the theoretical rate of NCO functions is reached by a return dosing.
Puis, on coule le contenu du récipient 2 dans le récipient 1. On maintient l’agitation pendant 60 minutes à 90 ± 1°C. On vérifie que le taux de fonction NCO est nul indiquant la fin de la réaction. Si celui-ci est non nul, la réaction est prolongée par période de 15 minutes jusqu’à achèvement de la réaction. Lorsque le taux atteint zéro, le composé T4 est formulé à l’aide d’un composé tensio-actif de type alcool éthoxylé (octanol éthoxylé avec dix équivalents d’oxyde d’éthylène) dans l’eau avec adjonction de 1 000 ppm d’un agent biocide (Biopol SMV Chemipol) et de 1 000 ppm d’un agent anti-mousse (Tego 1488 Evonik). On obtient une composition 4 constituée de 20 % en masse de composé T4 selon l’invention, de 10 % de composé tensio-actif et de 70 % en masse d’eau. Then, the contents of container 2 are poured into container 1. Stirring is maintained for 60 minutes at 90 ± 1°C. It is checked that the level of NCO function is zero indicating the end of the reaction. If this is non-zero, the reaction is prolonged for periods of 15 minutes until the reaction is complete. When the level reaches zero, compound T4 is formulated using an alcohol ethoxylate surfactant compound (octanol ethoxylated with ten equivalents of ethylene oxide) in water with the addition of 1000 ppm of a biocidal agent (Biopol SMV Chemipol) and 1000 ppm of an anti-foaming agent (Tego 1488 Evonik). A composition 4 is obtained consisting of 20% by mass of compound T4 according to the invention, 10% of surfactant compound and 70% by mass of water.
Exemple 1-5 : préparation d’un composé T5 selon l’invention Example 1-5: preparation of a compound T5 according to the invention
Dans un réacteur en verre de 3 L (récipient 1) équipé d’une agitation mécanique, d’une pompe à vide, d’une entrée d’azote et chauffé au moyen d’une double enveloppe dans laquelle circule de l’huile, on introduit 452,50 g de dodécanol éthoxylé avec 140 moles d’oxyde d’éthylène (MM = 6 355Da) que Ton chauffe à 90°C sous atmosphère inerte. Ce produit est déshydraté. Parallèlement, dans un ballon tricol en verre de 100 mF (récipient 2), on introduit 15,83 g d’IPDI auxquels on ajoute 400 ppm de catalyseur carboxylate de bismuth. On purge le milieu à l’azote puis on le chauffe jusqu’à 50°C. Forsque cette température est atteinte, on introduit progressivement 19,08 g de 4-dodécylcyclohexanol. Après addition complète, le mélange réactionnel est laissé sous agitation pendant 15 minutes. Puis, on vérifie que le taux théorique de fonctions NCO est atteint par un dosage en retour. In a 3 L glass reactor (receptacle 1) equipped with mechanical stirring, a vacuum pump, a nitrogen inlet and heated by means of a double jacket in which oil circulates, 452.50 g of dodecanol ethoxylated with 140 moles of ethylene oxide (MM=6355 Da) are introduced, which is heated to 90° C. under an inert atmosphere. This product is dehydrated. At the same time, 15.83 g of IPDI are introduced into a 100 mF three-necked glass flask (receptacle 2), to which 400 ppm of bismuth carboxylate catalyst are added. The medium is purged with nitrogen and then heated to 50°C. Forsque this temperature is reached, 19.08 g of 4-dodecylcyclohexanol are gradually introduced. After complete addition, the reaction mixture is left under stirring for 15 minutes. Then, it is verified that the theoretical rate of NCO functions is reached by a return dosing.
Puis, on coule le contenu du récipient 2 dans le récipient 1. On maintient l’agitation pendant 60 minutes à 90 ± 1°C. On vérifie que le taux de fonction NCO est nul indiquant la fin de la réaction. Si celui-ci est non nul, la réaction est prolongée par période de 15 minutes jusqu’à achèvement de la réaction. Forsque le taux atteint zéro, le composé T5 est formulé à l’aide d’un composé tensio-actif de type alcool éthoxylé (octanol éthoxylé avec dix équivalents d’oxyde d’éthylène) dans l’eau avec adjonction de 1 000 ppm d’un agent biocide (Biopol SMV Chemipol) et de 1 000 ppm d’un agent anti-mousse (Tego 1488 Evonik). On obtient une composition 5 constituée de 20 % en masse de composé T5 selon l’invention, de 10 % de composé tensio-actif et de 70 % en masse d’eau. Then, the contents of container 2 are poured into container 1. Stirring is maintained for 60 minutes at 90 ± 1°C. It is checked that the NCO function level is zero indicating the end of the reaction. If this is non-zero, the reaction is prolonged for periods of 15 minutes until the reaction is complete. When the level reaches zero, compound T5 is formulated using an alcohol ethoxylate surfactant compound (octanol ethoxylated with ten equivalents of ethylene oxide) in water with the addition of 1000 ppm of a biocidal agent (Biopol SMV Chemipol) and 1000 ppm of an antifoaming agent (Tego 1488 Evonik). A composition 5 is obtained consisting of 20% by mass of compound T5 according to the invention, 10% of surfactant compound and 70% by mass of water.
Exemple 2 : préparation de formulations de peinture selon l’invention On prépare les formulations de peinture Fl à F5 selon l’invention à partir respectivement des compositions aqueuses 1 à 5 de composés difonctionnels Tl à T5 selon l’invention. F’ ensemble des ingrédients et proportions (% en masse) mis en œuvre sont présentés dans le tableau 1. Example 2: preparation of paint formulations according to the invention The paint formulations F1 to F5 according to the invention are prepared from aqueous compositions 1 to 5 respectively of difunctional compounds T1 to T5 according to the invention. All the ingredients and proportions (% by mass) used are presented in Table 1.
Tableau 1 Exemple 3 : caractérisation de formulations de peinture selon l’invention Pour les formulations de peinture selon l’invention, on a déterminé, 24 h après leur préparation, la viscosité Brookfield, mesurée à 25°C et à 10 tr/min et à 100 tr/min (pBkio et PBkioo en mPa.s) au moyen d’un viscosimètre Brookfield DV-1 à mobiles de type RVT. Les propriétés des formulations de peinture sont présentées dans le tableau 2. Table 1 Example 3 Characterization of Paint Formulations According to the Invention For the paint formulations according to the invention, 24 hours after their preparation, the Brookfield viscosity was determined, measured at 25° C. and at 10 rpm and at 100 rev/min (p Bki o and PBkioo in mPa.s) using a Brookfield DV-1 viscometer with RVT type spindles. The properties of the paint formulations are shown in Table 2.
Tableau 2 Table 2
Les composés difonctionnels selon l’invention sont très efficaces pour obtenir d’excellentes viscosités à bas et moyens gradients de cisaillement pour des compositions de peinture. The difunctional compounds according to the invention are very effective in obtaining excellent viscosities at low and medium shear gradients for paint compositions.
Exemple 4 : caractérisation de formulations de peinture selon l’invention Pour les formulations de peinture selon l’invention, on a déterminé, 24 h après leur préparation et à température ambiante, la viscosité Cône Plan ou viscosité ICI, mesurée à haut gradient de cisaillement (pi en mPa.s), au moyen d’un viscosimètre Cône & Plate Research Equipment London (REL) à échelle de mesure de 0 à 5 poises, et la viscosité Stormer, mesurée à moyen gradient de cisaillement (pS en Krebs Units ou KU), au moyen du module standard d’un viscosimètre Brookfield KU-2. Les propriétés des formulations de peinture sont présentées dans le tableau 3. Tableau 3 Example 4 Characterization of Paint Formulations According to the Invention For the paint formulations according to the invention, the Cone Plane viscosity or ICI viscosity, measured at high shear gradient, was determined 24 hours after their preparation and at room temperature. (pi in mPa.s), using a Cone & Plate Research Equipment London (REL) viscometer with a measurement scale of 0 to 5 poises, and the Stormer viscosity, measured at a medium shear rate (pS in Krebs Units or KU), using the standard module of a Brookfield KU-2 viscometer. The properties of the paint formulations are shown in Table 3. Table 3
Les composés difonctionnels selon l’invention permettent de préparer des formulations de peinture dont les viscosités sont particulièrement bien contrôlées. Notamment, la viscosité mi est particulièrement élevée et le rapport mi/ps est alors excellent. Les composés selon l’invention permettent un excellent compromis entre la viscosité à haut gradient de cisaillement et la viscosité à bas gradient de cisaillement. The difunctional compounds according to the invention make it possible to prepare paint formulations whose viscosities are particularly well controlled. In particular, the viscosity mi is particularly high and the ratio mi/ps is then excellent. The compounds according to the invention allow an excellent compromise between the viscosity at high shear gradient and the viscosity at low shear gradient.

Claims

REVENDICATIONS
1. Composé difonctionnel T préparé par réaction : a. d’un équivalent molaire d’au moins un composé (a) non-alcoxylé choisi parmi : 1. Difunctional compound T prepared by reaction: a. a molar equivalent of at least one non-alkoxylated compound (a) chosen from:
- les composés monoisocyanates (al) aliphatiques linéaires comprenant de 6 à 40 atomes de carbone non-alcoxylés, - linear aliphatic monoisocyanate (al) compounds comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monoisocyanates (a2) aliphatiques ramifiés comprenant de 6 à 40 atomes de carbone non-alcoxylés, - branched aliphatic monoisocyanate compounds (a2) comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monoisocyanates (a3) cycloaliphatiques comprenant de 6 à 40 atomes de carbone non-alcoxylés, - cycloaliphatic monoisocyanate (a3) compounds comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monoisocyanates (a4) monoaromatiques comprenant de 6 à 30 atomes de carbone non-alcoxylés, - monoaromatic monoisocyanate compounds (a4) comprising from 6 to 30 non-alkoxylated carbon atoms,
- les composés monoisocyanates (a5) polyaromatiques comprenant de 10 à 80 atomes de carbone non-alcoxylés, - polyaromatic monoisocyanate compounds (a5) comprising from 10 to 80 non-alkoxylated carbon atoms,
- les composés monohalogénés (a6) aliphatiques linéaires comprenant de 6 à 40 atomes de carbone non-alcoxylés, - linear aliphatic monohalogen compounds (a6) comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monohalogénés (a7) aliphatiques ramifiés comprenant de 6 à 40 atomes de carbone non-alcoxylés, - branched aliphatic monohalogen compounds (a7) comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monohalogénés (a8) cycloaliphatiques comprenant de 6 à 40 atomes de carbone non-alcoxylés, - monohalogenated (a8) cycloaliphatic compounds comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monohalogénoalkylènes (a9) monoaromatiques comprenant de 7 à 30 atomes de carbone non-alcoxylés, - monoaromatic monohaloalkylene compounds (a9) comprising from 7 to 30 non-alkoxylated carbon atoms,
- les composés monohalogénoalkylènes (alO) polyaromatiques comprenant de 10 à 80 atomes de carbone non-alcoxylés, et b. d’un équivalent molaire d’au moins un composé (b) polyéthoxylé choisi parmi : - polyaromatic monohaloalkylene (alO) compounds comprising from 10 to 80 non-alkoxylated carbon atoms, and b. a molar equivalent of at least one polyethoxylated compound (b) chosen from:
- les monoalcools (bl) aliphatiques linéaires comprenant de 6 à 40 atomes de carbone polyéthoxylés comprenant strictement plus de 100 et jusqu’à 500 groupements oxyéthylène, - linear aliphatic monoalcohols (bl) comprising 6 to 40 polyethoxylated carbon atoms comprising strictly more than 100 and up to 500 oxyethylene groups,
- les monoalcools (b2) aliphatiques ramifiés comprenant de 6 à 40 atomes de carbone polyéthoxylés comprenant de 80 à 500 groupements oxyéthylène,- branched aliphatic monoalcohols (b2) comprising from 6 to 40 polyethoxylated carbon atoms comprising from 80 to 500 oxyethylene groups,
- les monoalcools (b3) cycloaliphatiques comprenant de 6 à 40 atomes de carbone polyéthoxylés comprenant de 80 à 500 groupements oxyéthylène, - les monoalcools (b4) monoaromatiques comprenant de 6 à 30 atomes de carbone polyéthoxylés comprenant strictement plus de 100 et jusqu’à 500 groupements oxyéthylène, - cycloaliphatic monoalcohols (b3) comprising from 6 to 40 polyethoxylated carbon atoms comprising from 80 to 500 oxyethylene groups, - monoaromatic monoalcohols (b4) comprising from 6 to 30 polyethoxylated carbon atoms comprising strictly more than 100 and up to 500 oxyethylene groups,
- les monoalcools (b5) polyaromatiques comprenant de 10 à 80 atomes de carbone polyéthoxylés comprenant de 80 à 500 groupements oxyéthylène. - polyaromatic monoalcohols (b5) comprising from 10 to 80 polyethoxylated carbon atoms comprising from 80 to 500 oxyethylene groups.
2. Composé difonctionnel T selon la revendication 1 pour lequel la réaction met en œuvre un unique composé (a) ou bien pour lequel la réaction met en œuvre deux ou trois composés (a) différents. 2. Difunctional compound T according to claim 1 for which the reaction implements a single compound (a) or else for which the reaction implements two or three different compounds (a).
3. Composé difonctionnel T selon l’une des revendications 1 ou 2 pour lequel le composé monohalogéné est choisi parmi un composé chloré, un composé bromé, un composé iodé et leurs combinaisons, de préférence le composé monohalogéné est un composé bromé. 3. Difunctional compound T according to one of claims 1 or 2 for which the monohalogen compound is chosen from a chlorine compound, a bromine compound, an iodine compound and combinations thereof, preferably the monohalogen compound is a bromine compound.
4. Composé difonctionnel T selon l’une des revendications 1 à 3 : 4. Difunctional compound T according to one of claims 1 to 3:
- pour lequel le degré de polyalcoxylation est compris entre 100 et 500, ou- for which the degree of polyalkoxylation is between 100 and 500, or
- pour lequel les monoalcools polyéthoxylés (bl) et (b3) comprennent de 105 à 400 groupements éthoxylés ou de 105 à 200 groupements éthoxylés, ou - pour lequel les monoalcools polyéthoxylés (b2), (b4) et (b5) comprennent de 80 à 400 groupements éthoxylés ou de 100 à 200 groupements éthoxylés, ou- for which the polyethoxylated monoalcohols (b1) and (b3) comprise from 105 to 400 ethoxylated groups or from 105 to 200 ethoxylated groups, or - for which the polyethoxylated monoalcohols (b2), (b4) and (b5) comprise from 80 to 400 ethoxylated groups or 100 to 200 ethoxylated groups, or
- pour lequel les composés (b) polyéthoxylés comprennent un nombre de groupements éthoxylés identiques ou différents. - for which the polyethoxylated compounds (b) comprise a number of identical or different ethoxylated groups.
5. Composé difonctionnel T selon l’une des revendications 1 à 4 pour lequel le composé5. Difunctional compound T according to one of claims 1 to 4 for which the compound
(a) est tel que : (a) is such that:
- la chaîne hydrocarbonée du composé (al) ou du composé (a6) comprend de 6 à 30 atomes de carbone, de préférence de 6 à 20 atomes de carbone ou de 8 à 16 atomes de carbone, plus préférentiellement le composé (al) ou le composé (a6) est choisi parmi n-octanyl non-alcoxylé, n-décanyl non-alcoxylé, n-dodécanyl non-alcoxylé, n-hexadécanyl non-alcoxylé, ou - the hydrocarbon chain of compound (al) or of compound (a6) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 16 carbon atoms, more preferably compound (al) or the compound (a6) is chosen from non-alkoxylated n-octanyl, non-alkoxylated n-decanyl, non-alkoxylated n-dodecanyl, non-alkoxylated n-hexadecanyl, or
- la chaîne hydrocarbonée du composé (a2) ou du composé (a7) comprend de 6 à 30 atomes de carbone, de préférence de 6 à 20 atomes de carbone ou de 8 à 16 atomes de carbone, plus préférentiellement le composé (a2) ou le composé (a7) est choisi parmi ethyl-hexanyl non-alcoxylé, iso-octanyl non-alcoxylé, iso-nonanyl non-alcoxylé, iso-décanyl non-alcoxylé, propyl-heptanyl non-alcoxylé, butyl-octanyl non-alcoxylé, iso-dodécanyl non-alcoxylé, iso-hexadécanyl non-alcoxylé, un groupement alkyl issu d’un alcool oxo non-alcoxylé, un groupement alkyl issu d’un alcool de Guerbet non-alcoxylé, ou- the hydrocarbon chain of compound (a2) or of compound (a7) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 16 carbon atoms, more preferably compound (a2) or the compound (a7) is chosen from non-alkoxylated ethyl-hexanyl, non-alkoxylated iso-octanyl, non-alkoxylated iso-nonanyl, non-alkoxylated iso-decanyl, non-alkoxylated propyl-heptanyl, non-alkoxylated butyl-octanyl, non-alkoxylated iso-dodecanyl, alkoxylated, non-alkoxylated iso-hexadecanyl, an alkyl group derived from a non-alkoxylated oxo alcohol, an alkyl group derived from a non-alkoxylated Guerbet alcohol, or
- la chaîne hydrocarbonée du composé (a3) ou du composé (a8) comprend de 6 à 30 atomes de carbone, de préférence de 6 à 20 atomes de carbone ou de 8 à 20 atomes de carbone, plus préférentiellement le composé (a3) ou le composé (a8) est choisi parmi ethyl-cyclohexanyl non-alcoxylé, n-nonyl-cyclohexanyl non-alcoxylé, n-dodécyl-cyclohexanyl non-alcoxylé, ou - the hydrocarbon chain of compound (a3) or of compound (a8) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 20 carbon atoms, more preferably compound (a3) or the compound (a8) is chosen from non-alkoxylated ethyl-cyclohexanyl, non-alkoxylated n-nonyl-cyclohexanyl, non-alkoxylated n-dodecyl-cyclohexanyl, or
- la chaîne hydrocarbonée du composé (a4) ou du composé (a9) comprend de 12 à 30 atomes de carbone ou de 12 à 22 atomes de carbone, de préférence le composé (a4) ou le composé (a9) est choisi parmi n-pentadocécyl-phényl non-alcoxylé ou- the hydrocarbon chain of compound (a4) or of compound (a9) comprises from 12 to 30 carbon atoms or from 12 to 22 carbon atoms, preferably compound (a4) or compound (a9) is chosen from n- non-alkoxylated pentadocecyl-phenyl or
- la chaîne hydrocarbonée du composé (a5) ou du composé (alO) comprend de 10 à 60 atomes de carbone, de préférence le composé (a5) ou le composé (alO) est choisi parmi naphtyl non-alcoxylé, distyryl-phényl non-alcoxylé, tristyryl-phényl non-alcoxylé, pentastyryl-cumyl-phényl non-alcoxylé. - the hydrocarbon chain of the compound (a5) or of the compound (alO) comprises from 10 to 60 carbon atoms, preferably the compound (a5) or the compound (alO) is chosen from non-alkoxylated naphthyl, non-alkoxylated distyryl-phenyl alkoxylated, non-alkoxylated tristyryl-phenyl, non-alkoxylated pentastyryl-cumyl-phenyl.
6. Composé difonctionnel T selon l’une des revendications 1 à 5 pour lequel le composé (b) est tel que : 6. Difunctional compound T according to one of claims 1 to 5 for which compound (b) is such that:
- la chaîne hydrocarbonée du composé (bl) comprend de 6 à 30 atomes de carbone, de préférence de 6 à 20 atomes de carbone ou de 8 à 16 atomes de carbone, plus préférentiellement le composé (bl) est choisi parmi n-octanol polyéthoxylé, n-décanol polyéthoxylé, n-dodécanol polyéthoxylé, n-hexadécanol polyéthoxylé, ou - the hydrocarbon chain of compound (bl) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 16 carbon atoms, more preferably compound (bl) is chosen from polyethoxylated n-octanol , polyethoxylated n-decanol, polyethoxylated n-dodecanol, polyethoxylated n-hexadecanol, or
- la chaîne hydrocarbonée du composé (b2) comprend de 6 à 30 atomes de carbone, de préférence de 6 à 20 atomes de carbone ou de 8 à 16 atomes de carbone, plus préférentiellement le composé (b2) est choisi parmi ethyl-hexanol polyéthoxylé, iso-octanol polyéthoxylé, iso-nonanol polyéthoxylé, iso-décanol polyéthoxylé, propyl-heptanol polyéthoxylé, butyl-octanol polyéthoxylé, iso-dodécanol polyéthoxylé, iso-hexadécanol polyéthoxylé, un alcool oxo polyéthoxylé, un alcool de Guerbet polyéthoxylé, ou - the hydrocarbon chain of compound (b2) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 16 carbon atoms, more preferably compound (b2) is chosen from polyethoxylated ethyl-hexanol , polyethoxylated iso-octanol, polyethoxylated iso-nonanol, polyethoxylated iso-decanol, polyethoxylated propyl-heptanol, polyethoxylated butyl-octanol, polyethoxylated iso-dodecanol, polyethoxylated iso-hexadecanol, a polyethoxylated oxo alcohol, a polyethoxylated Guerbet alcohol, or
- la chaîne hydrocarbonée du composé (b3) comprend de 6 à 30 atomes de carbone, de préférence de 6 à 20 atomes de carbone ou de 8 à 20 atomes de carbone, plus préférentiellement le composé (b3) est choisi parmi ethyl-cyclohexanol polyéthoxylé, n-nonyl-cyclohexanol polyéthoxylé, n-dodécyl-cyclohexanol polyéthoxylé, ou - the hydrocarbon chain of compound (b3) comprises from 6 to 30 carbon atoms, preferably from 6 to 20 carbon atoms or from 8 to 20 carbon atoms, plus preferably the compound (b3) is chosen from polyethoxylated ethyl-cyclohexanol, polyethoxylated n-nonyl-cyclohexanol, polyethoxylated n-dodecyl-cyclohexanol, or
- la chaîne hydrocarbonée du composé (b4) comprend de 12 à 30 atomes de carbone ou de 12 à 22 atomes de carbone, de préférence le composé (b4) est choisi parmi n-pentadocécyl-phénol polyéthoxylé ou - the hydrocarbon chain of compound (b4) comprises from 12 to 30 carbon atoms or from 12 to 22 carbon atoms, preferably compound (b4) is chosen from polyethoxylated n-pentadocecyl-phenol or
- la chaîne hydrocarbonée du composé (b5) comprend de 10 à 60 atomes de carbone, de préférence le composé (b5) est choisi parmi naphtol polyéthoxylé, distyryl-phénol polyéthoxylé, tristyryl-phénol polyéthoxylé, pentastyryl-cumyl-phénol polyéthoxylé. - the hydrocarbon chain of compound (b5) comprises from 10 to 60 carbon atoms, preferably compound (b5) is chosen from polyethoxylated naphthol, polyethoxylated distyryl-phenol, polyethoxylated tristyryl-phenol, polyethoxylated pentastyryl-cumyl-phenol.
7. Méthode de préparation d’un composé difonctionnel T par réaction : a. d’un équivalent molaire d’au moins un composé (a) non-alcoxylé choisi parmi :7. Method for preparing a difunctional compound T by reaction: a. a molar equivalent of at least one non-alkoxylated compound (a) chosen from:
- les composés monoisocyanates (al) aliphatiques linéaires comprenant de 6 à 40 atomes de carbone non-alcoxylés, - linear aliphatic monoisocyanate (al) compounds comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monoisocyanates (a2) aliphatiques ramifiés comprenant de 6 à 40 atomes de carbone non-alcoxylés, - branched aliphatic monoisocyanate compounds (a2) comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monoisocyanates (a3) cycloaliphatiques comprenant de 6 à 40 atomes de carbone non-alcoxylés, - cycloaliphatic monoisocyanate (a3) compounds comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monoisocyanates (a4) monoaromatiques comprenant de 6 à 30 atomes de carbone non-alcoxylés, - monoaromatic monoisocyanate compounds (a4) comprising from 6 to 30 non-alkoxylated carbon atoms,
- les composés monoisocyanates (a5) poly aromatique s comprenant de 10 à 80 atomes de carbone non-alcoxylés, - polyaromatic monoisocyanate compounds (a5) comprising from 10 to 80 non-alkoxylated carbon atoms,
- les composés monohalogénés (a6) aliphatiques linéaires comprenant de 6 à 40 atomes de carbone non-alcoxylés, - linear aliphatic monohalogen compounds (a6) comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monohalogénés (a7) aliphatiques ramifiés comprenant de 6 à 40 atomes de carbone non-alcoxylés, - branched aliphatic monohalogen compounds (a7) comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monohalogénés (a8) cycloaliphatiques comprenant de 6 à 40 atomes de carbone non-alcoxylés, - monohalogenated (a8) cycloaliphatic compounds comprising from 6 to 40 non-alkoxylated carbon atoms,
- les composés monohalogénoalkylènes (a9) monoaromatiques comprenant de 7 à 30 atomes de carbone non-alcoxylés, - monoaromatic monohaloalkylene compounds (a9) comprising from 7 to 30 non-alkoxylated carbon atoms,
- les composés monohalogénoalkylènes (alO) polyaromatiques comprenant de 10 à 80 atomes de carbone non-alcoxylés, et b. d’un équivalent molaire d’au moins un composé (b) polyéthoxylé choisi parmi : - les monoalcools (bl) aliphatiques linéaires comprenant de 6 à 40 atomes de carbone polyéthoxylés comprenant strictement plus de 100 et jusqu’à 500 groupements oxyéthylène, - polyaromatic monohaloalkylene (alO) compounds comprising from 10 to 80 non-alkoxylated carbon atoms, and b. of a molar equivalent of at least one polyethoxylated compound (b) chosen from: - linear aliphatic monoalcohols (bl) comprising from 6 to 40 polyethoxylated carbon atoms comprising strictly more than 100 and up to 500 oxyethylene groups,
- les monoalcools (b2) aliphatiques ramifiés comprenant de 6 à 40 atomes de carbone polyéthoxylés comprenant de 80 à 500 groupements oxyéthylène,- branched aliphatic monoalcohols (b2) comprising from 6 to 40 polyethoxylated carbon atoms comprising from 80 to 500 oxyethylene groups,
- les monoalcools (b3) cycloaliphatiques comprenant de 6 à 40 atomes de carbone polyéthoxylés comprenant de 80 à 500 groupements oxyéthylène, - cycloaliphatic monoalcohols (b3) comprising from 6 to 40 polyethoxylated carbon atoms comprising from 80 to 500 oxyethylene groups,
- les monoalcools (b4) monoaromatiques comprenant de 6 à 30 atomes de carbone polyéthoxylés comprenant strictement plus de 100 et jusqu’à 500 groupements oxyéthylène, - monoaromatic monoalcohols (b4) comprising from 6 to 30 polyethoxylated carbon atoms comprising strictly more than 100 and up to 500 oxyethylene groups,
- les monoalcools (b5) polyaromatiques comprenant de 10 à 80 atomes de carbone polyéthoxylés comprenant de 80 à 500 groupements oxyéthylène. - polyaromatic monoalcohols (b5) comprising from 10 to 80 polyethoxylated carbon atoms comprising from 80 to 500 oxyethylene groups.
8. Méthode selon la revendication 7 pour la préparation d’un composé difonctionnel T selon l’une des revendications 2 à 6. 8. Method according to claim 7 for the preparation of a difunctional compound T according to one of claims 2 to 6.
9. Composition aqueuse comprenant : 9. Aqueous composition comprising:
- au moins un composé choisi parmi un composé difonctionnel T selon l’une des revendications 1 à 6 et un composé difonctionnel T préparé selon la méthode de préparation des revendications 7 ou 8, et éventuellement - at least one compound chosen from a difunctional compound T according to one of claims 1 to 6 and a difunctional compound T prepared according to the method of preparation of claims 7 or 8, and optionally
- au moins un additif choisi parmi : - at least one additive chosen from:
• un composé amphiphile, notamment un composé tensio-actif, de préférence un composé tensio-actif hydroxylé, par exemple alkyl-polyalkyleneglycol, notamment alkyl-polyethyleneglycol et alkyl-polypropyleneglycol ; • an amphiphilic compound, in particular a surfactant compound, preferably a hydroxylated surfactant compound, for example alkyl-polyalkylene glycol, in particular alkyl-polyethylene glycol and alkyl-polypropylene glycol;
• un dérivé de polysaccharide, par exemple cyclodextrine, dérivé de cyclodextrine, polyéthers, alkyl-glucosides ; • a polysaccharide derivative, for example cyclodextrin, cyclodextrin derivative, polyethers, alkyl-glucosides;
• solvants, notamment solvants de coalescence, et composés hydrotropes, par exemple glycol, butylglycol, butyldiglycol, monopropyleneglycol, ethyleneglycol, ethylenediglycol, produits Dowanol dont le numéro CAS est 34590-94-8), produits Texanol dont le numéro CAS est 25265-77-4) ; • solvents, in particular coalescence solvents, and hydrotropic compounds, for example glycol, butylglycol, butyldiglycol, monopropyleneglycol, ethyleneglycol, ethylenediglycol, Dowanol products whose CAS number is 34590-94-8), Texanol products whose CAS number is 25265-77 -4);
• agents anti-mousse, agents biocides. • anti-foaming agents, biocidal agents.
10. Formulation aqueuse comprenant : - au moins une composition selon la revendication 9 ; éventuellement 10. Aqueous formulation comprising: - at least one composition according to claim 9; eventually
- au moins un pigment organique ou minéral ou des particules organiques, organo-métalliques ou minérales, par exemple carbonate de calcium, talc, kaolin, mica, silicates, silice, oxydes métalliques, notamment dioxyde de titane, oxydes de fer ; et éventuellement - at least one organic or mineral pigment or organic, organo-metallic or mineral particles, for example calcium carbonate, talc, kaolin, mica, silicates, silica, metal oxides, in particular titanium dioxide, iron oxides; and eventually
- au moins un agent choisi parmi un agent espaceur de particules, un agent dispersant, un agent stabilisant stérique, un agent stabilisant électrostatique, un agent opacifiant, un solvant, un agent de coalescence, un agent anti-mousse, un agent de conservation, un agent biocide, un agent d’étalement, un agent épaississant, un copolymère filmogène et leurs mélanges. - at least one agent chosen from a particle spacer, a dispersing agent, a steric stabilizing agent, an electrostatic stabilizing agent, an opacifying agent, a solvent, a coalescing agent, an anti-foaming agent, a preservative, a biocidal agent, a spreading agent, a thickening agent, a film-forming copolymer and mixtures thereof.
11. Formulation selon la revendication 10 de revêtement, notamment une formulation d’encre, une formulation de vernis, une formulation d’adhésif, une formulation de peinture, par exemple de peinture décorative ou de peinture industrielle. 11. Formulation according to claim 10 of coating, in particular an ink formulation, a varnish formulation, an adhesive formulation, a paint formulation, for example decorative paint or industrial paint.
12. Pâte pigmentaire aqueuse concentrée comprenant au moins un composé difonctionnel T selon l’une des revendications 1 à 6 ou au moins un composé difonctionnel T préparé selon la méthode de préparation des revendications 7 ou 8 et au moins un pigment coloré organique ou minéral. 12. Concentrated aqueous pigment paste comprising at least one difunctional compound T according to one of claims 1 to 6 or at least one difunctional compound T prepared according to the method of preparation of claims 7 or 8 and at least one organic or inorganic colored pigment.
13. Méthode de contrôle de la viscosité d’une composition aqueuse comprenant l’addition d’au moins un composé difonctionnel T selon l’une des revendications 1 à 6 ou d’au moins un composé difonctionnel T préparé selon la méthode de préparation des revendications 7 ou 8. 13. Method for controlling the viscosity of an aqueous composition comprising the addition of at least one difunctional compound T according to one of claims 1 to 6 or of at least one difunctional compound T prepared according to the method for preparing claims 7 or 8.
14. Méthode selon la revendication 13 pour laquelle la composition aqueuse est une composition selon la revendication 9 ou bien une formulation définie selon l’une des revendications 10 et 11. 14. Method according to claim 13 for which the aqueous composition is a composition according to claim 9 or else a formulation defined according to one of claims 10 and 11.
EP21758397.0A 2020-07-27 2021-07-26 Rheology-modifying difunctional compound Pending EP4188976A1 (en)

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FR2007895A FR3112786B1 (en) 2020-07-27 2020-07-27 DIFUNCTIONAL RHEOLOGY MODIFIER COMPOUND
PCT/FR2021/000085 WO2022023626A1 (en) 2020-07-27 2021-07-26 Rheology-modifying difunctional compound

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US4301083A (en) * 1977-04-04 1981-11-17 Kuraray Co., Ltd. Preparation of etherified polyoxyalkylene derivatives
EP0295031A3 (en) * 1987-06-12 1991-05-08 SMITH &amp; NEPHEW plc Orthopaedic splinting material
JPH06322392A (en) * 1993-05-07 1994-11-22 Asahi Denka Kogyo Kk Slow solubilizing agent
KR100404774B1 (en) * 1995-09-06 2004-04-01 아사히 덴카 고교 가부시키가이샤 Viscosity regulator
FR3057871B1 (en) * 2016-10-20 2018-11-02 Coatex URETHANE COMPOUND MODIFIER OF RHEOLOGY
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FR3112786A1 (en) 2022-01-28
CN115776999A (en) 2023-03-10
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US20230331665A1 (en) 2023-10-19
FR3112786B1 (en) 2023-12-29

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